With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.35700-40-4,2,3-Dihydrobenzofuran-7-carboxylic acid,as a common compound, the synthetic route is as follows.
A solution of 2,3-dihydrobenzofuran-7-carboxylic acid (1.0g, 6.09 mmol, 1.0 equiv.), dimethylmethoxyamine hydrochloride (654 mg, 6.7 mmol, 1.1 equiv.), diisopropylethylamine (DIEA) (2.35 ml, 13.4 mmol, 2.2 equiv.), benzotriazole-1-yl-oxy-tris-pyrrolidinophosphonium hexafluorophosphate (PyBOP) (3.48g, 6.7 mmol, 1.1equiv.) and 4-dimethylaminopyridine (DMAP) (74 mg, 0.67 mmol, .1 equiv.) in anhydrous THF (20 ml) was stirred for 18hr under argon. The reaction mixture was then diluted with EtOAc (100 ml) and washed with aqueous sat. NaHCO3 (2×150 ml) and aqueous 1N HCl (2 x 150 ml), the oragnic layer was dried over MgSO4, filtered and solvent removed. yield : 1.06 mg, 84 %. LS-MS calcd 207, found 208. To a solution of the amide (950 mg, 4.59 mmol, 1.0 equiv.) in anhydrous THF (20 ml) was cooled to -5C under argon, was slowly added 1.0 M LAH in THF (9.1 ml, 9.14 mmol, 1.5 equiv.), the reaction mixture was stirred for 1 hr at -5C- A solution of aqueous 1 N HCl (150 ml) was slowly added to the reaction mixture, and extracted with EtOAc (50 ml). The organic layer was washed with aqueous 1 N HCl (150 ml), the organic layer was collected and dried over MgSO4, filter and solvent removed under reduced pressure to yield the aldhyde. Yield: 620 mg, 91%. LR-MS calcd 148, found 149.
35700-40-4, The synthetic route of 35700-40-4 has been constantly updated, and we look forward to future research findings.
Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; EP1041980; (2005); B1;,
Benzofuran – Wikipedia
Benzofuran | C8H6O – PubChem