Synthesis of euparin and dehydrotremetone was written by Ramachandran, P. K.;Chang, T.;Horton, W. J.. And the article was included in Tetrahedron Letters in 1963.Application In Synthesis of Methyl benzofuran-2-carboxylate This article mentions the following:
Me 5-acetyl-6-acetoxycoumarilate ketalized with (CH2OH)2 with the loss of the O-Ac group, and the product treated with excess MeMgI and chromatographed on Al2O3 yielded euparin (I), m. 121-2°; semicarbazone m. 254-5°; dinitrophenylhydrazone m. 254-5°; maleic anhydride adduct m. 244-5°. I gives a green color with FeCl3 and an orange to red, brown, and then green color with concentrated H2SO4. Me coumarilate (II) acetylated in the presence – of AlCl3 yielded the 5-Ac derivative (III) of II, the oxime of which was converted by a Bechmann rearrangement to the 5-NH2 derivative (IV) of II. IV was then converted to the 5-Cl derivative of II, m. 94-6°. The catalytic reduction of III yielded the 5-Et derivative of II. The ethylene glycol ketal of III treated with MeMgI, and the resulting tertiary alc. dehydrated and cleaved by acid yielded dehydrotremetone (V), m. 84.0-5.5°; oxime m. 131.53.5°; maleic anhydride adduct m. 205-10°. The synthetic V was identical with V from Aplopappus heterophyllus and from Eupatorium urticaefolium. In the experiment, the researchers used many compounds, for example, Methyl benzofuran-2-carboxylate (cas: 1646-27-1Application In Synthesis of Methyl benzofuran-2-carboxylate).
Methyl benzofuran-2-carboxylate (cas: 1646-27-1) belongs to benzofurans derivatives. Benzofurans are compounds with a planar structure having 10 pi electrons that include the lone pair on oxygen atom, which makes it more susceptible to electrophilic attack. Benzofurans have also made significant and distinctive contributions to biology. They exhibit several biological activities that range from antioxidant, antitubercular, antiplasmodial, insecticidal.Application In Synthesis of Methyl benzofuran-2-carboxylate
Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem