El-Gezawy, Hani et al. published their research in Journal of Physical Chemistry B in 2005 |CAS: 53724-96-2

The Article related to photoactive yellow protein photochem photophys chromophore model bridged compound, General Biochemistry: Proteins and Their Constituents and other aspects.HPLC of Formula: 53724-96-2

On October 6, 2005, El-Gezawy, Hani; Rettig, Wolfgang; Danel, Andrzej; Jonusauskas, Gediminas published an article.HPLC of Formula: 53724-96-2 The title of the article was Probing the Photochemical Mechanism in Photoactive Yellow Protein. And the article contained the following:

Selectively bridged model compounds related to the chromophore in photoactive yellow protein have been synthesized where the single bond adjacent to the benzene ring (bond 1) and where both bond 1 and the adjacent double bond (bond 2) are bridged. They were compared to the nonbridged reference compound regarding their photophys. properties using steady-state and time-resolved fluorescence at various temperatures Quantum chem. calculations were addnl. performed and showed that several conformers are populated in the ground state. The neutral model compounds show that the nonradiative deactivation channel is linked to both single- and double-bond twisting. The relative importance of single-bond twisting is increased for the corresponding deprotonated hydroxy compounds with an enhanced donor character. The simultaneous photochem. activity of both single and double bonds explains the ease of photochem. isomerization in the confined environment of the natural PYP protein and also of the primary step in the vision process in rhodopsin. The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).HPLC of Formula: 53724-96-2

The Article related to photoactive yellow protein photochem photophys chromophore model bridged compound, General Biochemistry: Proteins and Their Constituents and other aspects.HPLC of Formula: 53724-96-2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Hong, Hui et al. published their patent in 2009 |CAS: 53724-96-2

The Article related to pyridine phenylpiperidinyloxy derivative preparation metabolic disorder, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Electric Literature of 53724-96-2

On May 22, 2009, Hong, Hui; Xu, Xiang; Yu, Jiaxin; Singh, Rajinder; Darwish, Ihab S.; Thota, Sambaiah published a patent.Electric Literature of 53724-96-2 The title of the patent was Preparation of phenylpiperidinyloxypyridine derivatives for use as therapeutic agents in metabolic disorders. And the patent contained the following:

Title compounds I [B = substituted aryl or heteroaryl; E = CO, SO2, or bond; T = alkyl-OR10, alkyl-C(O)R10, alkyl-S(O)p, etc.; Y = (un)substituted amine; each R4 independently = halo, CN. NO2, alkyl, etc.; or two R4 on the same carbon optionally combine to form oxo; R10 = H, alkyl, haloalkyl, etc.; m = 0 to 4; n = 0 to 3; p = 0 to 2; provided that when B = Ph, then E is not CO], and their pharmaceutically acceptable salts, are prepared and disclosed as therapeutic agents in metabolic disorders. Thus, e.g., II was prepared by deprotection of tert-Bu 1-(pyridin-4-ylmethyl)piperidin-4-ylcarbamate followed by amidation with 6-chloropicolinic acid, and etherification with 1-(4-(trifluoromethyl)phenyl)piperidin-4-ol. Select I were evaluated for their ability to activate AMPK using enzyme-linked immunosorbent assays, e.g., II demonstrated an EC50 value of 0.1-0.5 μM. The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).Electric Literature of 53724-96-2

The Article related to pyridine phenylpiperidinyloxy derivative preparation metabolic disorder, Heterocyclic Compounds (One Hetero Atom): Pyridines and other aspects.Electric Literature of 53724-96-2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Nilsson, Magnus et al. published their patent in 2005 |CAS: 53724-96-2

The Article related to oxohexahydrofuropyrrole amino acid amide preparation cathepsin k inhibitor, osteoporosis gingivitis periodontitis pagets disease treatment amino acid amide, Amino Acids, Peptides, and Proteins: Amino Acids and other aspects.Recommanded Product: Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate

On July 21, 2005, Nilsson, Magnus; Zhou, Xiao-Xiong; Oden, Lourdes; Classon, Bjorn; Noren, Rolf; Grabowska, Urszula; Jackson, Philip; Fallon, Philip; Carr, Andrew; Liley, Mark; Tozer, Matt; Johnson, Tony; Diaz, Victor; Crespo, Laia; Kangasmetsa, Jussi; Bonnaud, Thierry published a patent.Recommanded Product: Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate The title of the patent was Preparation of N- oxohexahydrofuropyrrole amino acid amides as cathepsin K inhibitors.. And the patent contained the following:

Title compounds [I; 1 of R1, R2 = halo, the other = H, halo; R3 = (fluoro)alkyl; R4 = H; R3R4C = (substituted) spirocycloalkyl, heterocyclyl; R5 = H, Me; E = CO, SOm, NR5SOm, NR5CO, CO2; R6 = stable (substituted) mono- or bicyclic carbocyclyl, heterocyclyl; m = 0-2], were prepared Thus, title compound (II) (multistep preparation given) inhibited cathepsin K with Ki = 5.3 nM. The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).Recommanded Product: Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate

The Article related to oxohexahydrofuropyrrole amino acid amide preparation cathepsin k inhibitor, osteoporosis gingivitis periodontitis pagets disease treatment amino acid amide, Amino Acids, Peptides, and Proteins: Amino Acids and other aspects.Recommanded Product: Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Macmillan, J. et al. published their research in Journal of the Chemical Society in 1959 |CAS: 53724-96-2

Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas:53724-96-2) belongs to benzofuran. Benzofuran is the “parent” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Related Products of 53724-96-2

Macmillan, J. published an article in 1959, the title of the article was Griseofulvin. XVI. Synthesis of compounds related to griseofulvin.Related Products of 53724-96-2 And the article contains the following content:

Racemic spirans related to griseofulvin (I) were prepared by condensation between coumarones and dibromoalkanes (II). The presence of the grisan ring synthesis in I was confirmed by synthesis of 7-chloro-4,6-dimethoxy-2′-methylgrisan-3-one (III), which was shown to be the racemate of the l,d-stereoisomer, obtained by degrading the l,d-diastereoisomer of I (the prefixes denote the configuration of the 2 asym. centers, the spiran center preceding; I is the d,d-stereoisomer, inversion of the spiran center giving the l,d-diastereoisomer). The synthesis of racemates of some non-spiran oxidation products, and improved preparations of some II, were also described. (All m.ps. are corrected; ultraviolet spectra determined in EtOH solution) NaBr (109 g.) and 137 ml. concentrated H2SO4 in 125 ml. H2O kept at 30° during the gradual addition of 43 g. tetrahydro-2-methylfuran, the mixture boiled 2 hrs., steam distilled, the distillate extracted with Et2O, and the extract fractionated gave 103 g. CH2Br(CH2)2CHBrMe (IV), b25 98-9°, n15D 1.516. (a) CH2Br(CH2)3CHBrMe (V), b100 153-5°, was prepared in 1.2% over-all yield according to Perkin [J. Chem. Soc. 51, 702(1887)]. (b) PBr3 (182 g.) and then 120 g. Br added in portions to 140 g. 1-benzoyl-2-methylpiperidine, m. 46°, at 0° with shaking, the product distilled in vacuo until the distillate became yellow, the distillate shaken with 500 g. ice, the mixture extracted with petr. ether (VI), the extract washed with aqueous Na2CO3, H2O, and concentrated H2SO4 until the washings were colorless, concentrated, and the residue distilled gave 103 g. V, b23 121-4°. Dry HCl passed into a solution of 72.0 g. m-C6H4(OH)2, 48 g. CH2ClCN, and 48 g. ZnCl2 in dry Et2O 2 hrs. at room temperature, after 1 hr. the precipitate filtered off, washed with Et2O, hydrolyzed 1 hr. at 70° with 5 l. H2O, the mixture cooled, and the product crystallized (PhMe) gave 85 g. 2,4-(HO)2C6H3COCH2Cl (VII), in. 132-3°. (a) VII (30 g.) in 300 ml. Et2O treated with CH2N2-Et2O and the precipitate crystallized (EtOH) gave 31 g. 5,2-MeO(ClCH2CO)C6H3OH (VIII), m. 116-17°. (b) Powd. AlCl3 (9 g.) added to 8.0 g. m-C6H4(OMe)2 and 6.5 g. CH2ClCOCl in 30 ml. CS2, after 1 hr. CS2 decanted from a red oil, the oil treated with 30 ml. ice-cold H2O and 20 ml. concentrated HCl, steam distilled, and the steam distillate worked up gave 3.9 g. VIII, m. 116-17°. (a) 6-Hydroxy-3-coumaranone (5.0 g.) in 2 l. C6H6 and excess CH2N2-Et2O kept 18 hrs. and the neutral product recovered gave 4.2 g. 6-methoxy compound (IX), m. 124-5°, ν 1710 cm.-1, λ 318, 268, 233, 208 mμ (log ε 4.00, 4.12, 4.05, 4.29). (b) VIII (3.0 g.) and 3.0 g. NaOAc in 150 ml. EtOH heated 2 hrs. and the product crystallized gave 2.2 g. IX, m. 124-5°. IX (0.82 g.) in 50 ml. C6H6 added (during 30 min.) simultaneously with 1.15 g. IV in 50 ml. C6H6 to a stirred and refluxing suspension of 1.4 g. Me3COK (X) in 50 ml. C6H6, the mixture refluxed 3 hrs., cooled, the filtered solution washed with aqueous NaOH and H2O, evaporated, the residue chromatographed in C6H6 on Al2O3, a blue band eluted with C6H6, the recovered oil (300 mg.) rechromatographed in VI, eluted with 20:1 Et2O-VI, and the gum crystallized from petr. ether gave 36 mg. 6-methoxy-3-oxocoumaran-2-spiro-1′-(2′-methylcylopentane), m. 167-8° (sublimation in vacuo and recrystallization from EtOH), ν 1712 cm.-1, λ 318, 267, 233, 208 mμ (log ε 4.01, 4.12, 4.05, 4.29). 7-Chloro-4,6-dimethoxy-3-coumaranone (XI) (2.29 g.) in 50 ml. C6H6 treated as above with 2.8 g. X in 50 ml. C6H6, refluxed 5 hrs., cooled, filtered, the filtrate extracted with aqueous NaOH, and the extract acidified gave 60 mg. 3,2,4,6-Cl(HO)(MeO)2C6HAc, m. 189-91°; the semisolid (recovered from the neutral fraction) repeatedly extracted with VI, the solid (400 mg.) recovered from the extract sublimed at 110°/10-4 mm., and the sublimate crystallized (EtOH) gave 7-chloro-4,6-dimethoxy-3-oxocoumaran-2-spirocydopentane, m. 192-3°, ν 1717 cm.-1, λ 331, 322, 289, 238, 213 mμ (log ε 3.68, 3.69, 4.30, 4.20, 4.37); the VI-insoluble material chromatographed and sublimed gave 1.08 g. XI, m. 212-14°. XI (2.29 g.) in 50 ml. C6H6 condensed with 2.31 g. Br(CH2)5Br in 50 ml. C6H6 in the presence of 2.8 g. X in 50 ml. C6H6 as above, the residual gum treated with C6H6-VI, the precipitated solid (120 mg.) sublimed at 130°/10-4 mm., and the sublimate recrystallized (EtOH) gave 70 mg. 7-chloro-4,6-dimethoxygrisan-3-one, m. 176-7°, ν 1715 cm.-1; 1.20 g. XI was recovered from the C6H6-VI mother liquor. XI (2.90 g.) condensed as above with 2.44 g. V in the presence of 2.80 g. X (identical volumes C6H6 used), refluxed 1.5 hrs., cooled, the filtered solution washed with aqueous NaOH, concentrated to 5 ml., diluted with 5 ml. VI, and the solution kept at 0° deposited 112 mg. precipitate (XII); the gum recovered from the mother liquor chromatographed in C6H6 on Al2O3 and eluted with C6H6 gave, from a yellow band, 40 mg. gum, which, sublimed (120-30°/10-4 mm.) and crystallized (EtOH), afforded 25 mg. compound (XIII), and, from a blue band, 340 mg. gum, which, crystallized (C6H6-VI), yielded 295 mg. compound (XIV); XII, XIII, and XIV combined, sublimed (110-20°/10-4 mm.), and crystallized (EtOH) gave 405 mg. III, m. 157-8°, λ 331, 322, 289, 238, 212 mμ (log ε 3.67, 3.70, 4.33, 4.20, 4.41). XI (11.45 g.) in 200 ml. C6H6 condensed with 12.25 g. MeCHBr(CH2)2COBr in 100 ml. C6H6 in the presence of 14 g. X in 100 ml. C6H6 as above, the C6H6 solution extracted with aqueous NaOH, evaporated, and chromatographed gave 1.3 g. 7-chloro-4,6-dimethoxycoumaron-3-yl- γ-bromovalerate, m. 124°, ν 1760, 1623, 1609 cm.-1, λ 265 and 219 mμ (log ε 4.18, 4.62). XI (4.2 g.) in 200 ml. dioxane treated at 46° with 2.1 g. MeCH:CHCO2Me (XV) and 8.0 ml. N MeONaMeOH, kept 6 hrs. at 55-60° and 2 days at room temperature, the filtered solution treated with 5 ml. AcOH and C, filtered, and the filtrate evaporated in vacuo; the residue dissolved in 150 ml. C6H6, the solution washed with H2O, dried, chromatographed on Al2O3, eluted with 100:1 C6H6-MeOH, the recovered product distilled (170-200°/10-4 mm.) on to a cold finger, and the material crystallized gave 1.0 g. product (XVI); the material recovered from the mother liquor extracted with Me2CO gave 0.5 g. product (XVII); XVI and XVII combined and washed with Me2CO gave 1.00 g. α-ester (XVIII), Me 7-chloro-4,6-dimethoxy-3-oxocoumaran-2-β-butyrate, m. 152-4° (C6H6-VI); the gum recovered from the mother liquors fractionally crystallized (Et2O) gave 0.8 g. impure material and 0.90 g. β-XVIII, m. 83-6°, m.p. not depressed with (-)-β-XVIII prepared from I (see below). β-XVIII (100 mg.), 0.5 g. anhydrous K2CO3, and 10 ml. Me2CO refluxed 7 hrs. and the product fractionally crystallized (C6H6-VI) gave 36 mg. α-XVIII, m. 150-2°; crystallization of the more soluble fractions from Et2O gave 41 mg. β-XVIII, m. 83-5°. Similar results were obtained with α-XVIII. (1) α-XVIII (561 mg.) and 25 ml. N HCl boiled 3 hrs. (20 ml. H2O added after 2.5 hrs.), the precipitate (495 mg.) filtered off, and washed with H2O gave (-)-7-chloro-4,6-dimethoxy-3-oxocoumaran-2-β-butyric acid (XIX), m. 154-62° (decomposition). (2) Hydrolysis of 500 mg. β-XVIII in the same way gave 460 mg. XIX. XIX treated with CH2N2 gave a mixture separated by crystallization into 47 mg. α-XVIII, m. 142-50°, and 38 mg. β-XVIII, m. 82-5°. XIX (234 mg.) and 10 ml. N NaOH boiled 4 hrs., cooled, filtered, the filtrate acidified, the precipitate (123 mg.) collected, and crystallized (EtOAc) gave 7-chloro-6-hydroxy-4-methoxy-3-oxocoumaran-2-β-butyric acid, m. 212-14° (decomposition), ν (CHCl3) 1701 and 1737 cm.-1 XIX (134 mg.) in 10 ml. N Na2CO3 treated at 1-2° during 1.5 hrs. with 3.0 ml. 4.5% aqueous KMnO4, the mixture kept 1.5 hrs. at 0°, excess decomposed with SO2, the filtered solution acidified with HCl, the gummy product (isolated with Et2O) treated with a little Et2O, and the resultant solid (85 mg.) crystallized from EtAc-petr. ether gave the 2-OH derivative (XX), m. 189-90° (decomposition). XX (85 mg.), 0.3 ml. Ac2O, and 0.7 ml. C5H5N kept 3 days at 35°, diluted with H2O at 0°, and the product washed with aqueous NaHCO3 and H2O gave the lactone (XXI), m. 223-4° (EtOAc). XXI was also obtained by subliming XX at 190-210°/10-4 mm. N MeONa-MeOH (2.0 ml.) added to 1.94 g. 4,6-dimethoxy-3-coumaranone (XXII) and 1.00 g. XV in 40 ml. dioxane at 24°, after 24 hrs. the mixture acidified with AcOH, evaporated in vacuo, the residue taken up in Et2O, the solution washed with aqueous NaHCO3, and H2O, evaporated, the oily product chromatographed in Et2O on Al2O3, and a blue band eluted with 100:1 Et2O-MeOH gave 1.7 g. sirup (XXIII); 2.3 g. XXIII from several experiments kept with Et2O gave 1.0 g. α-ester, Me 4,6-dimethoxy-3-oxocoumaran-2-β-butyric acid (XXIV) Me ester (XXV), m. 88-9° (C6H6Et2O); the sirup from the Et2O mother liquor distilled (180-210°/10-3 mm.) gave essentially β-XXV, sirup. 2N EtONa-EtOH (0.43 ml.) added to 1.00 g. XXII and 0.59 g. MeCH:CHCO2Et in 18 ml. dioxane at 20° after 48 hrs. the mixture filtered, the filtrate acidified with AcOH, the product recovered, chromatographed, eluted like XXV, and the oil (1.00 g.) distilled (190°/10-3 mm.) gave XXIV Et ester (XXVI), oil. XXVI (1.9 g.) and 20 ml. 3N HCl boiled 5 hrs., the cooled mixture made alk., washed with Et2O, acidified, the product (1.19 g.) extracted with Et2O, and the extract distilled (200°/10-3 mm.) gave XXIV, containing a phenolic impurity. XXIV (350 mg.) in 22 ml. N Na2CO3 treated at 1-2° during 2 hrs. with 7.6 ml. 4.5% aqueous KMnO4 and worked up gave 70 mg. 2-OH derivative (XXVII), m. 169-73° (decomposition). Dehydration of XXVII as above gave the lactone (XXVIII), m. 150-1° (EtOAc-petr. ether). An ice-cold suspension of 525 mg. XXVI in 30 ml. N Na2CO3 treated dropwise with 5% aqueous KMnO4 (only a few drops decolorized), 25 ml. dioxane added, 10.0 ml. 5% aqueous KMnO4, added in 1 hr., the mixture kept overnight at 0°, decolorized with SO2, filtered, the filtrate and Me2CO washings of the filter cake evaporated in vacuo, aqueous NaOH added to the residue, the mixture extracted with Et2O (0.2 g. XXVI recovered from the extract), acidified, the product extracted with Et2O, and crystallized (Et2O and then EtAc) gave 34 mg. XXVIII, m. 150-1°. (-)-XIX from I gave (-)-β-XVIII, m. 96-8° (Et2O), [α]22D -19° ± 3° (c 0.84, Me2CO). The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).Related Products of 53724-96-2

Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas:53724-96-2) belongs to benzofuran. Benzofuran is the “parent” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Related Products of 53724-96-2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

MacMillan, J. et al. published their research in Journal of the Chemical Society in 1959 |CAS: 53724-96-2

Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas:53724-96-2) belongs to benzofuran. Benzofuran is the “parent” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Product Details of 53724-96-2

MacMillan, J. published an article in 1959, the title of the article was Griseofulvin. XVII. Synthesis of 7-chloro-4,6-dimethoxy-2′-methylgrisan-3,4′-dione.Product Details of 53724-96-2 And the article contains the following content:

The synthesis is described of grisan and 3-coumaranone spirocyclopentane analogs of some griseofulvin (I) derivatives and of racemates of some I degradation products. (All m.ps. are corrected; absorption spectra determined in EtOH.) Et 6-hydroxy-3-methylcoumarone-2-carboxylate (II), m. 179° (EtOH), ν 1700 cm.-1, λ 313, 282, 241, 210 mμ (log ε 4.30, 4.07, 3.90, 4.24), was prepared in 60% yield by the method of Hantzsch [Ber. 19, 292(1886)]. Treatment of II with Me2SO4 gave 30% 6-methoxy-3-methylcoumarone-2-carboxylic acid (III), m. 184°, and 25% III Et ester (IV), m. 74-5°, ν 1700 cm.-1, λ 312, 285, 243 mμ (log ε 4.44, 4.13, 3.97); esterification of III gave IV. 6-Methoxy-3-methylcoumarone-2-acetic acid (V) chloride and AcCH(MgOEt)CO2Et (VI) gave Et α-acetyl-β-oxo-6-methoxy-3-methylcoumarone-2-γ-butyrate (VII), oil, ν 1714, 1623, and 1587 cm.-1; Cu derivative (VIII), m. 175° (MeOH), ν 1715, 1692, 1671, 1587 cm.-1 VII (7 g.) and 15 mL. concentrated H2SO4 kept 3 days at -5°, diluted with 50 mL. H2O, extracted with Et2O, the Et2O solution extracted with aqueous NaHCO3, and the alk. extract acidified gave 200 mg. V, m. 139-40°; recovery from the Et2O solution gave a pale yellow oil (IX). IX in EtOH passed through a C column, the resulting material triturated for a long time under petr. ether (X) at -50°, and the solid further recrystallized at room temperature gave 2.8 g. Et 6-methoxy-3-methylenecoumaran-2-spiro-1′-(2′-methyl-4′-oxocyclopent-2′-en-3′-carboxylate) (XI), m. 122°, ν 1745, 1707, 1649, 1615, 1595 cm.-1, λ 327, 263, 231, 214 mμ (log ε 3.98, 4.12, 4.35, 4.31); 2,4-dinitrophenylhydrazone, m. 175-6° (C6H6-X). Cyclization of VIII with H2SO4 gave 45% XI. XI (150 mg.) hydrogenated at room temperature and pressure with a catalyst prepared in situ from 7 mg. PdCl2 and 75 mg. C in 10 mL. AcOH (1 mol H absorbed), the recovered gum chromatographed in Et2O on Al2O3, eluted with Et2O, and the product repeatedly triturated with X at 0° gave 105 mg. corresponding 3-Me analog, m. 77-8°, ν 1738, 1698, 1610 cm.-1, λ 320, 302, 281, ∼263,228 mμ (log ε 2.78, 3.45, 3.59, 3.72, 4.25); 2,4-dinitrophenylhydrazone, m. 160° (C6H6-petr. ether). A stream of O3-O passed into 500 mg. XI in 30 mL. CCl4 until the solution became opaque, the filtered solution evaporated, the residual gum mixed with 25 mL. H2O, kept 24 h., and the aqueous phase distilled into saturated dimedon (XII) solution in 10% aqueous alc. gave XII derivative of CH2O, m. 191-2°; an Et2O solution of the residual gum chromatographed on Al2O3, the lowest bright-blue fluorescent band eluted with Et2O and the recovered product boiled with X (110 mg. solid obtained); the solid combined with 100 mg. slightly impure material from the following band fluorescing greenish-blue and recrystallized (petr. ether) gave 200 mg. corresponding 3-oxo compound (XIII), m. 115-17°, ν 1751, 1715, and 1701 cm.-1, λ 321, 275, 232 mμ (log ε 3.98, 4.21, 4.23); mono-2,4-dinitrophenylhydrazone, m. 243° (decomposition) (C6H6-petr. ether). Oxidation of 100 mg. XIII with Fehling’s solution gave 25 mg. 2,4-HO(MeO)C6H3CO2H, m. 154-5°. XIII (70 mg.) and 17.5 mL. 2N HCl and 14 mL. EtOH refluxed 6 h. under N cooled (15 mg. solid separated), EtOH removed in vacuo (15 mg. solid and 30 mg. XIII separated), the combined product purified through the Na salt, and recrystallized (EtOH) gave 23 mg. corresponding acid (XIV), m. 175-7°, ν 1716 and 1697 cm.-1, λ 318, 273, 232, 210 mμ (log ε 4.05, 4.25, 4.30, 4.45). XIV (70 mg.) heated 10 min. at 190-200° in an N atm., the residue sublimed in situ in vacuo, and the sublimate recrystallized (aqueous Me2CO) gave 40 mg. 6-methoxy-3-oxocoumaran-2-spiro-1′-(2′-methylcyclopent-2′-en-4′-one) (XV), m. 193-5°, ν 1713 cm.-1, λ 320, 273, 232, 209 mμ (log ε 3.92, 4.07, 4.16, 4.40); mono-2,4-dinitrophenylhydrazone, m. 238-40° (EtOAc). XV (15 mg.) in 1.5 mL. EtOAc added to a previously catalyst prepared from 10 mg. PdCl2 and 40 mg. C in 1 mL H2O, the mixture shaken with H at room temperature and pressure until absorption ceased (2.4 mol H absorbed in 5 min.), and the product (XVI) (13 mg.) recovered; XVI (13 mg.) chromatographed in C6H6 on Al2O3, a bright-blue fluorescent band eluted with C6H6, the product (2 mg.) recovered, sublimed, and crystallized (petr. ether) gave 0.8 mg. 6-methoxy-3-oxocoumaran-2-spiro-1′-(2′-methylcyclopentane), m. 167-8°, identical with the product from condensation of 6-methoxycoumaran-3-one and CH2Br(CH2)2CHBrMe (cf. preceding abstract). β-Propiolactone (XVII) (8.64 g.) and 19.44 g. 6-methoxy-3-methylcoumarone refluxed 6 h. at 200°, the cooled residue ground with aqueous Na2CO3, the mixture filtered, the Et2O-washed filtrate acidified, the precipitate filtered off, sublimed in vacuo, and the sublimate crystallized (dilute EtOH) gave 4.9 g. 6-methoxy-3-methyl-coumarone-2-β-propionic acid (XVIII), m. 137°, ν 1707 cm.-1, λ 292 and 253 mμ (log ε 3.80, 4.16). 6-Methoxy-3-methylcoumarone-2-acetic acid (440 mg.) and 1 mL. SOCl2 was warmed gently until a clear solution was obtained, volatiles removed in vacuo below 30°, the residual oil in 10 mL. Et2O added at 0° to a 3-fold excess CH2N2 in 15 mL. Et2O, the solution kept 24 h. at 0°, and the Et2O removed in vacuo; the residual crude diazo ketone (m. 118-23°) in 10 mL. dioxane added dropwise with stirring to 2 g. Ag2O in 1 g. Na2S2O3 and 1 g. K2CO3 in 20 mL. H2O at 50-60° (N evolved), after 20 min. the mixture heated 10 min. at 70° and 5 min. at 90°, filtered, the filtrate acidified with dilute HNO3, the oil triturated with H2O, the resulting semisolid sublimed in vacuo, and the sublimate crystallized (dilute EtOH) gave 60 mg. XVIII, m. 137-8°. XVIII treated with PCl5 gave the acid chloride (XIX), green oil; amide, plates (C6H6-petr. ether). XIX in 500 mL. Et2O mixed with a suspension of VI [from 2.7 g. AcCH2CO2Et (XX), 1.2 mL. EtOH, and 0.48 g. Mg in 50 mL. Et2O], the mixture refluxed 24 h., excess dilute AcOH added, the separated Et2O layer washed with aqueous NaHCO3 (from the alk. wash 200 mg. XVIII was isolated on acidification), concentrated, the oil (4.2 g.) chromatographed in C6H6 on Al2O3 and eluted with C6H6 gave, from a narrow fluorescent band, 90 mg. oil, which, on crystallization (petr. ether), afforded 60 mg. XVIII Et ester (XXI), m. 51-2°, ν 1737, 1624, 1594 cm.-1, identical with material obtained by esterifying XVIII, and, from a greenish-red band, 3.1 g. oil, which, heated 4 h. at 100-10°/10-4 mm., yield 2.2 g. crude oxo ester (XXII), giving an intense Fe+++ reaction in EtOH and forming a Cu chelate. Crude XXII (12 g.) in 25 mL. concentrated H2SO4 kept 8 days at 0°, worked up as described above for the lower homolog, and the alk. extract acidified gave a yellow precipitate which decomposed on filtration; the unfiltered mixture extracted with C6H6, the extract passed through silica, and eluted with C6H6 gave 600 mg. XVIII, m. 133-5°; the Et2O solution concentrated, the oil (4.5 g.) chromatographed in Et2O on Al2O3, and eluted with Et2O gave, from a narrow band, 20 mg. XXI, and, from a pale blue band, 4.1 g. oil, which, crystallized (EtOH) and recrystallized (aqueous EtOH), afforded 3.8 g. Et 6-methoxy-2′-methyl-3-methylene-4′-oxogris-2′-ene-3′-carboxylate (XXIII), m. 97-8°, ν 1728, 1668, 1641, 1614 cm.-1, λ 326, 316, 273, 260, 233, 215 mμ (log ε 4.05, 4.09, 4.18, 4.43, 4.37); 2,4-dinitrophenylhydrazone, m. 182° (decomposition). Crude XXII (1.5 g.) mixed with 20 g. polyphosphoric acid (XXIV), kept 4 days at room temperature, and worked up gave 700 mg. XXIII, 30 mg. XXI, and no acidic product. XXIII (1.0 g.) in 30 mL. CCl4 ozonized as above (CH2O isolated with XII), the product chromatographed in Et2O on Al2O3, the yellow gum (510 mg.) treated with EtOH, seeded, and the solid recrystallized (dilute EtOH) gave Et 6-methoxy-2′-methyl-3,4′-dioxogris-2′-ene-3′-carboxylate (XXV), m. 110-11°, ν 1735, 1704, 1686 cm.-1, λ 320, 272, 231, 208 mμ (log ε 3.95, 4.12, 4.17, 4.42), giving an intractable precipitate with Brady reagent. XXV (3 g.) refluxed 4 h. in an N atm. with 300 mL. EtOH and 350 mL. 2N HCl (0.6 mol CO2 evolved), the solution concentrated in vacuo, the aqueous residue extracted with Et2O, the extract washed with aqueous NaHCO3 (recovery gave only a trace of acidic gum), concentrated, the residual oil (1.6 g.) chromatographed in Et2O on Al2O3, and eluted with Et2O gave, from a blue band, 1.5 g. 6-methoxy-2′-methylgris-2′-ene-3,4′-dione, gum, ν 1713 and 1667 cm.-1, λ, 318, 272, 232, 209 mμ (log ε 3.98, 4.13, 4.22, 4.45) [2,4-dinitrophenylhydrazone, m. 230° (EtOAc)], and, from a dark blue band, 20 mg. XXV. 3,2,4,6-Cl(HO)(MeO)2C6HAc (XXVa) (46.0 g.), 66.4 g. CH2BrCO2Et, and 56.0 g. anhydrous K2CO3 in 700 mL. Me2CO refluxed 72 h., filtered, the filtrate evaporated in vacuo, the oil dissolved in 200 mL. EtOH, the solution treated with Et2O, and the precipitate recrystallized (EtOH) gave 56.6 g. 2,6,3,5-Ac(Cl)-(MeO)2C6HOCH2CO2Et (XXVI), m. 72°, ν 1763, 1735, 1684 cm.-1, λ 305, 292, 258, 223 mμ (log ε 3.35, 3.43, 3.70, 4.21); 2,4-dinitrophenylhydrazone m. 136° (EtOAc). With CH2-BrCO2Me in the above experiment, there was obtained the corresponding Me ester (XXVII), m. 103-4° (MeOH), ν 1760 and 1680 cm.-1, λ 305, 293, 268, 233 mμ (log ε 3.35, 3.42, 3.66, 4.20). XXVI (47.4 g.) in 200 mL. EtOH, 300 mL. H2O, and 14 mL. H2SO4 refluxed 4 h., diluted with H2O until cloudy, kept overnight at 5%, the precipitate filtered off, washed with aqueous Na2CO3 (19.7 g. XXVI remained), and the alk. extract acidified gave 19.1 g. acid (XXVIII), m. 144° (C5H6 or H2O), ν 1751 and 1659 cm.-1, λ 301, 292, 258, 224 mμ (log ε 3.42, 3.39, 3.66, 4.19). XXVII (500 mg.) and 20 mL. 3N HCl refluxed 6.5 h., the solid filtered off, dissolved in warm aqueous Na2CO3, the solution treated with C, filtered, and the filtrate acidified at 0° gave 311 mg. XXVIII cyclic form (XXIX) (R = H) (XXX), m. 143-4° (dilute EtOH), ν 1746 cm.-1, λ 275 and 240 mμ (log ε 3.09, 3.95); mixtures of XXVIII and XXX m. 115-40°; a 1:1 mixture (XXXI), m. 119-20°, behaved as a pure compound (see below). XXVII (1.5 g.) and 75 mL. N HCl refluxed 4 h. and worked up gave 1.1 g. XXX, m. 119-20° (C6H6), ν 1749 and 1659 cm.-1, identical with a 1:1 mixture XXVIII and XXX. XXX (29 mg.) in 5 mL. Et2O treated overnight with 1 mol CH2N2 in 5 mL. Et2O and worked up gave 24 mg. XXIX (R = Me) (XXXII), m. 97° (MeOH), ν 1742 cm.-1, λ ∼275 and 235 mμ (log ε 3.07, 3.98). XXVIII treated similarly gave the isomeric open-chain acid (XXXIII), m. 103-4°, mixed m.p. with XXXII 78-85°. XXXIII or XXXII (17.3 g.), 34 g. fused NaOAc, and 100 mL. Ac2O heated under reflux until CO2 evolution ceased (30 min.), the cooled solution diluted with H2O, made alk. with Na2CO3, the product filtered off, passed through a column of Al2O3 in 3 l. C6H6 recovered, and crystallized (EtOH) gave 14 g. 7-chloro-4,6-dimethoxy-3-methylcoumarone (XXXIV), m. 148°, ν 1626, 1611, 1591 cm.-1, λ 320, ∼275, 263, 220, 216 mμ (log ε 2.42, 4.00, 4.19, 4.56, 4.56). XXVI (15.8 g.) refluxed 1 h. with 1 g. Na in 50 mL. EtOH, the cooled solution diluted with 750 mL. H2O, the precipitate (2.7 g.) filtered off, and crystallized (EtOH) gave Et 7-chloro-4,6-dimethoxy-3-methylcoumarone-2-carboxylate (XXXV), m. 172-3°, ν 1712 cm.-1, λ 312, 298, 245, 230 mμ (log ε 4.32, 4.37, 4.34, 4.30); acidification of the filtrate with dilute HCl gave 11.2 g. XXVIII, m. 143°. XXXV (895 mg.) warmed 10 min. at 40° with 6 g. NaOH in 100 mL. 50% aqueous EtOH, diluted with ice and H2O, the solution acidified, and the precipitate (790 mg.) sublimed in vacuo gave the corresponding acid (XXXVI), m. 310° (decomposition), ν, 1671 cm.-1, λ 293 and 238 mμ (log ε 4.26, 4.31); Me ester, m. 196° (MeOH). XXXVI converted to the acid chloride (SOCl2 plus C5H5N) and the latter treated with CH2N2-Et2O gave the diazo ketone (XXXVII), m. 118-20° (Et2O). Attempted Wolff rearrangement of 600 mg. XXXVII as above gave 530 mg. XXXVI, m. 250-60° (decomposition). XXXVI (200 mg.) in 0.5 mL. quinoline heated 5 min. at 190-5° with 100 mg. Cu bronze and worked up gave 150 mg. XXXIV, m. 143°. Anhydrous HCN (200 mL.) added to 142 g. XXXIV in 6 1. Et2O at 0°, a fast stream of dry HCl passed in at 0-5° until absorption ceased (6 h.), the solution kept overnight at 0°, the aldimine-HCl (XXXVIII) filtered off, washed with Et2O, heated with 10 1. H2O at 100%, and the product (XXXIX) (110 g.) filtered off (after 24 h. a second crop XXXVIII separated from the Et2O mother liquor which yielded 27 g. addnl. XXXIX on hydrolysis); XXXIX in C6H6 passed through Al2O3, crystallized (C6H6, EtOH, or Me2CO), sublimed, and the sublimate recrystallized (Me2CO) gave the 2-OHC derivative (XL) m. 183°, μ 1662 cm.-1, λ 341, 312, 253 mμ (log ε 4.24, 4.16, 4.28) [2,4-dinitrophenylhydrazone m. 312°(Me2CO); azlactone m. 235°(EtOAc), giving on alk. hydrolysis 7-chloro-4,6-dimethoxy-2,3-dimethylcoumarone (XLI), m. 290° (MOH), μ and 1596 cm.-1]. XL oxidized with KMn-O4 in aqueous Me2CO gave XXXVI, m. 310° (decomposition). XL (2.26 g.) and 720 mg. XVII refluxed 4 h., cooled, the melt dissolved in 200 mL. Et2O, the solution filtered, the filtrate extracted with aqueous Na2CO3, and the alk. extract acidified gave 720 mg. 7-chloro-4,6-dimethoxy-3-methylcoumarone-2-β-propionic acid (XLII), m. 123-30° (chromatog. followed by recovery from the Ag salt); a sample of XLII was converted by Et2O-CH2N2 to the Me ester (XLIII), m. 102° (MeOH), ν 1739 cm.-1, λ 320, 294, 278, 265, 226, 223 mμ (log ε 2.61, 3.30, 4.05, 4.27, 4.53, 4.52, 4.52). The remaining XLII (500 mg.) methylated as above, the product chromatographed in C6H6 on Al2O3, a pale-blue band eluted with Et2O, the recovered ester (350 mg.) hydrolyzed with N alc. HCl, the compound sublimed in vacuo, and recrystallized (aqueous EtOH) gave XLII, m. 134-5°, ν (Nujol mull) 1722 and 1706 cm.-1, (in CHCl3) 1716 cm.-1 XXXIX (4 g.), 6.7 g. CH2(CO2H)2, 330 mg. piperidine, and 17 mL. C5H5N heated 1 h. at 100° and then 10 min. at 120°, The cooled solution was acidified, the precipitate (6.1 g.) extracted with aqueous Na2CO3 (1.3 g. XXXIV remained), and the alk. extract acidified gave 4.75 g. 7-chloro-4,6-dimethoxy-3-methylcoumarone-2-acrylic acid (XLIV), m. 252° (C6H6), ν 1692 and 1676 cm.-1, λ 329 and 255 mν (log ε 4.44, 4.04); Me ester, m. 179° (MeOH), ν 1709 cm.-1 (a) XLIV (102 mg.) in 50 mL. AcOH added to 0.2 g. Raney Ni in 2 mL. EtOH, hydrogenated at room temperature and pressure until absorption ceased (1 mol H absorbed in 8 h.), the mixture filtered, the filtrate concentrated to 5 mL. in vacuo, 100 mL. H2O added, stored overnight at 5°, the solid (60 mg.) collected, stirred 1 h. with cold dilute HCl, the mixture filtered, the precipitate (35 mg.) purified through the Na salt, and crystallized (petr. ether) gave XLII, identical with XLII as prepared above. (b) Crude XLIV (93 g.) in 3.5 1. 0.1N NaOH hydrogenated at room temperature and pressure in the presence of 50 g. 5% Pd-SrCO3 (absorption ceased after 8 h. when 0.64 mol H was absorbed), 10 g. C added, the filtered solution acidified (38 g. solid obtained and an addnl. 5 g. by repptg. the sticky material from aqueous NaOH), and the product chromatographed in C6H6 on silica gave 39 g. XLII, m. 133-5°, identical with XLII prepared in a. (c) XLIV (56 g., m. 252°) in 2.3 1. 0.1N NaOH hydrogenated as in b (2 mol H absorbed in 1 h.), the acidified solution extracted with Et2O, the extracts concentrated, the combined solids therefrom treated with CH2N2-Et2O, the resulting oil (50.7 g.) chromatographed in C6H6 on Al2O3, and a single bright blue band eluted with C6H6 gave 6.3 g. product (XLV), needles, m. 104-6° (C6H6-petr. ether), and 3.6 g. product (XLVI), prisms, m. 98-100° (MeOH), and, on further elution, 37 g. gum (XLVII). XLV crystallized (MeOH) gave Me 7-chloro-4,6-dimethoxy-3-methylcoumaran-2-β-propionate, prisms, m. 107-8°, ν 1731 cm.-1, hydrolyzed with boiling N NaOH to the corresponding acid, m. 147-8°, ν 1716 cm.-1 XLVI recrystallized (MeOH) gave 2.7 g. XLIII, m. 102°, alk. hydrolysis giving 1.9 g. XLII. XLVII rechromatographed, the single band eluted in 10 equal fractions with C6H6, and fractions 2 and 8 rechromatographed; fraction 2 gave essentially Me 4,6-dimethoxy-3-methylcoumaran-2-β-propionate (XLVIII), uncrystallizable gum, ν 1728 cm.-1, alk. hydrolysis yielding the acid (XLIX), m. 114° (1:1 Et2O-petr. ether); fraction 8 hydrolyzed with NaOH, the product crystallized (1:1 C6H6-petr. ether), the crystals hand-picked, and recrystallized gave 4,6-dimethoxy-3-methylcoumarone-2-β-propionic acid (L), m. 124°. XLIX (2 g.) and 200 mg. S heated 20 min. at 220° and 5 min. at 280°, the product continuously extracted with X, and the resulting crystallized extract hand-picked gave 320 mg. recovered XLIX and 540 mg. L, m. 124°. XLVIII (157 mg.) and 135 mg. ο-chloranil in 5 mL. CHCl3 stored 1.5 h. in the dark, the recovered product chromatographed in C6H6 on Al2O3, the pale blue band eluted with C6H6, and the product (135 mg.) crystallized (1:1 Et2O-petr. ether and then MeOH) gave the coumarone-tetrachloropyrocatechol complex (LI), m. 117°. LI hydrolyzed by alkali and the product crystallized (1:1 Et2OX) gave L, m. 122-4°. XLII (23.5 g.) in 500 mL. dry CHCl3 treated with 20 g. PCl5, the mixture refluxed 0.5 h., volatile products removed at 30° in vacuo, and the residue (LII) kept 4 h. at 12 mm., LII dissolved in 1.5 l. Et2O, 12 g. VI added, the mixture refluxed 24 h., 250 mL. 40% AcOH added, the Et2O layer separated, extracted with Na2CO3 solution (the extract afforded 5.9 g. XLII), and concentrated; the residual oil (25 g.) chromatographed in Et2O on Al2O3 and eluted gave, from a bright-blue band, 800 mg. XLII Et ester (LIII), m. 74-6° (EtOH), and, from an orange-red band, 18 g. orange oil (LIV). LIV heated 2 h. at 110°/10-4 mm. (excess XX removed) gave 14 g. gum (LV), giving a red color with alc. FeCl3 and forming no stable ketonic derivatives LV (12 g.) in 100 mL. Et2O shaken with saturated aqueous Cu(OAc)2 deposited 2.8 g. blue crystals (LVI); the Et2O layer evaporated and the residual gum fractionally crystallized gave 6 g. product (LVII) and 1.8 g. Et α-acetyl-β-oxo-7-chloro-4,6-dimethoxy-3-methylcoumarone-2-γ-carboxylate (LVIII) β-Cu chelate (LIX), m. 98-100° (EtOH), converted to the α-Cu isomer (LX) on continued heating at 120-30°; LVI and LVII combined and crystallized (CHCl3) gave LX, m. 164°. (a) LIX (1.4 g.) and 20 g. XXIV kept 10 days at room temperature, diluted with 50 mL. ice and H2O, extracted with Et2O, the extract washed with aqueous Na2CO3, dried, evaporated, the residual gum (1.18 g.) chromatographed in C6H6 on Al2O3, and the column eluted with C6H6 gave (1) from a narrow blue band, 5 mg. LIII, m. 72-3°, (2) from a greenish-blue band, a gum, which, kept in EtOH, deposited 175 mg. product (LXI), m. 137° and (3) from a blue band, a gum, which, kept in X, deposited 278 mg. product (LXII), m. 129-31°. LXI and LXII combined, recrystallized (EtOH), the crystals (410 mg.) sublimed in vacuo, and the sublimate recrystallized (MeOH) gave Et 7-chloro-4,6-dimethoxy-2′-methyl-3-methylene-4′-oxogris-2′-ene-3′-carboxylate (LXIII), m. 137°, ν 1731, 1680, 1638, 1610 cm.-1, λ282, ∼275, and 253 mμ (log ε 4.30, 4.28, 4.57). (b) LX (500 mg.) and 20 g. XXIV heated 1 h. at 70-80° and worked up as above gave 210 mg. LXIII, m. 137°. (c) LX (1.8 g.) and 30 g. XXIV kept 10 days at room temperature, worked up as above, and the alk. extract acidified gave 600 mg. XLII; some Cu derivative (600 mg.) was regenerated by shaking the acid with aqueous Cu(OAc)2; the remaining gum (320 mg.) chromatographed gave 120 mg. LIII and 5 mg. unidentified compound, m. 181-2° (MeOH). LXIII (248 mg.) in 15 mL. CCl4 ozonized 8 min. at room temperature, CCl4 removed in vacuo, the residue in 20 mL. Et2O and 10 mL. AcOH cooled in ice, treated with 2 mL. H2O and 100 mg. Zn dust, after 12 h. 20 mL. H2O added, the Et2O layer separated, combined with Et2O-washings of the aqueous layer, and worked up gave 5% LXIII, 40% XXVa, 30% Cl-free acidic fraction, and 4% 7-chloro-4,6-dimethoxy-2′-methylgris-2′-ene-3,4′-dione (LXIV), m. 167-8°, ν 1718 and 1683 cm.-1, λ 323, 291, 235, 213 mμ (log ε 3.70, 4.30, 4.19, 4.42). LXIII (137 mg.) in CCl4 ozonized 0.5 h. and worked up gave 10 mg. Cl-free solid, 30 mg. XXVa, 6 mg. LXIII, 1.2 mg. unidentified product, m. 143-9°, and 13 mg. Et 7-chloro-4,6-dimethoxy-3,4′-dioxogris-2′-ene-3′-carboxylate, m. 174° (EtOH), ν 1739, 1705, 1684, 1623, 1593 cm.-1, not hydrolyzed by boiling 1-10N HCl, alk. hydrolysis causing degradation LXIV (10 mg.) in 1 mL. EtOAc added to a previously reduced catalyst prepared from 5 mg. PdCl2 and 20 mg. C in 1 mL. H2O, shaken 6 h. with H at room temperature and pressure (absorption complete in 3 h.), the recovered gum chromatographed in C6H6 on Al2O3, and the recovered gums from each eluate chromatographed on circular paper gave an alc. fraction (not investigated) and the racemate of l,d-7-chloro-4,6-dimethoxy-2′-methylgrisan-3-one, d,d-7-chloro-4,6-dimethoxy-2′-methylgrisan-3,4′-dione, m. 170-5°. The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).Product Details of 53724-96-2

Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas:53724-96-2) belongs to benzofuran. Benzofuran is the “parent” of many related compounds with more complex structures. For example, psoralen is a benzofuran derivative that occurs in several plants. Product Details of 53724-96-2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Royer, Rene et al. published their research in European Journal of Medicinal Chemistry in 1974 |CAS: 53724-96-2

The Article related to benzofurancarboxylate nitration acetylation, structure activity nitrobenzofuran, amebicide nitro benzofurancarboxylate, trichomonacide nitro benzofurancarboxylate, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.Safety of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate

Royer, Rene; Lamotte, Genevieve; Demerseman, Pierre; Platzer, Nicole; Cavier, Raymond published an article in 1974, the title of the article was Nitro derivatives of biological interest. VIII. Comparative orientations of nitration and acetylation of 3-methyl-4-methoxyl ethyl coumarilates.Safety of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate And the article contains the following content:

Nitration of the 4 methoxycoumarilates I occurred mainly in the benzene ring, although in some cases the nitromethyl derivative was also detected. I were also acetylated in the benzene ring and the acetylated or nitrated esters hydrolyzed and decarboxylated, and the decarboxylation products again nitrated. Only the 2-nitro derivatives were amebicides and trichomonacides. The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).Safety of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate

The Article related to benzofurancarboxylate nitration acetylation, structure activity nitrobenzofuran, amebicide nitro benzofurancarboxylate, trichomonacide nitro benzofurancarboxylate, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.Safety of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Suzuki, Tsuneo et al. published their research in Journal of Heterocyclic Chemistry in 1992 |CAS: 53724-96-2

The Article related to acetylphenoxyacetate cyclization, phenoxyacetate acetyl cyclization, benzofuran, tetrahydrobenzoxepindione, benzoxepindione tetrahydro, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.SDS of cas: 53724-96-2

On April 30, 1992, Suzuki, Tsuneo; Tanemura, Kiyoshi; Horaguchi, Takaaki; Shimizu, Takahachi; Sakakibara, Tohru published an article.SDS of cas: 53724-96-2 The title of the article was Benzofuran derivatives. Part 4. Synthesis of benzofurans and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones. And the article contained the following:

By treatment of Et 4- or 5-substituted 2-acetylphenoxyacetates I (R = 4-Me, H, 5-Cl, etc.) with potassium hydroxide in dry dioxane, benzofurans II-VII and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones VIII were obtained. The relative yields of benzofurans II-VII and 2,3,4,5-tetrahydro-1-benzoxepin-3,5-diones VIII varied with the types of 4- or 5-substituents. The electron-donating 4-methoxy group favored the formation of benzoxepins. On the other hand, electron-withdrawing substituents such as the 4-nitro group favored the formation of benzofurans. When esters I were treated with sodium amide, 2,3-dihydrobenzofurans II were obtained exclusively regardless of 4- or 5-substituents. The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).SDS of cas: 53724-96-2

The Article related to acetylphenoxyacetate cyclization, phenoxyacetate acetyl cyclization, benzofuran, tetrahydrobenzoxepindione, benzoxepindione tetrahydro, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.SDS of cas: 53724-96-2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Chen, Wei et al. published their research in Organic & Biomolecular Chemistry in 2017 |CAS: 53724-96-2

The Article related to benzofuran carboxaldehyde nitromethane copper acetate catalyst enantioselective henry reaction, benzofuryl nitro ethanol preparation, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.Formula: C13H14O4

Chen, Wei; Zhou, Zhao-Hui; Chen, Hong-Bin published an article in 2017, the title of the article was Efficient synthesis of chiral benzofuryl β-nitro alcohols via a catalytic asymmetric Henry reaction.Formula: C13H14O4 And the article contains the following content:

Chiral β-amino alc. ligands were found to be effective for the copper(II)-catalyzed asym. Henry reaction of benzofuran-2-carboxaldehydes with nitromethane, which led to the formation of (S)-enriched benzofuryl β-nitro alcs. with satisfactory enantioselectivities (up to 98% ee). The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).Formula: C13H14O4

The Article related to benzofuran carboxaldehyde nitromethane copper acetate catalyst enantioselective henry reaction, benzofuryl nitro ethanol preparation, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.Formula: C13H14O4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Rene, Loic et al. published their research in Bulletin de la Societe Chimique de France in 1975 |CAS: 53724-96-2

The Article related to benzofuranol formyl, demethylation methoxybenzofuran pyridine hydrochloride, quinoline demethylation solvent, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.Formula: C13H14O4

Rene, Loic; Buisson, Jean P.; Royer, Rene published an article in 1975, the title of the article was Reactions induced by pyridinium halides. XX. First examples of dealkylation by pyridinium hydrochloride in quinoline.Formula: C13H14O4 And the article contains the following content:

Benzofuranols I-VI (R = R1 = H, R2 = H, Me) were prepared in improved yields by demethylating I-VI (R1 = Me) with pyridine-HCl in quinoline. I-VI (R1 = Me) were prepared by formylating coumarilic acid esters, hydrolyzing I-VI (R = CO2Me, CO2Et, R1 = Me), and decarboxylating I-VI (R = CO2H). The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).Formula: C13H14O4

The Article related to benzofuranol formyl, demethylation methoxybenzofuran pyridine hydrochloride, quinoline demethylation solvent, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.Formula: C13H14O4

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem

Suzuki, Tsuneo et al. published their research in Nippon Shika Daigaku Kiyo, Ippan Kyoiku-kei in 1990 |CAS: 53724-96-2

The Article related to acetylphenoxyacetate cyclization hydroxide, benzofuran derivative, benzoxepindione derivative, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.Computed Properties of 53724-96-2

On March 31, 1990, Suzuki, Tsuneo published an article.Computed Properties of 53724-96-2 The title of the article was The reaction of ethyl (2-acetyl-5-methoxyphenoxy)acetate with potassium hydroxide. And the article contained the following:

The reaction of title ester I (R = Et) with KOH gave benzofurans, benzoxepindione II, and I (R = H). The experimental process involved the reaction of Ethyl 6-methoxy-3-methylbenzofuran-2-carboxylate(cas: 53724-96-2).Computed Properties of 53724-96-2

The Article related to acetylphenoxyacetate cyclization hydroxide, benzofuran derivative, benzoxepindione derivative, Heterocyclic Compounds (One Hetero Atom): Areno- and Diarenofurans and other aspects.Computed Properties of 53724-96-2

Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem