Ethyl Acetate → HCID 9800843, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 4-[isopropyl-(7-t-butyl-3,3,6-trimethyl-2,3-dihydro-benzofuran-5-yl)-amino]-benzoic acid methyl ester (Compound 69, 0.015 g, 0.038 mmol) in 3 mL of ethanol was treated with 1M sodium hydroxide (1.5 mL, 1.5 mmol) and the resulting clear solution was heated at 80° C. for 2 hours. The volatiles were removed by distillation in vacuo and the residue was neutralized with saturated ammonium chloride solution and extracted with diethylether. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated to afford, after flash column chromatography using 25% ethyl acetate in hexanes as the eluent, the title compound (0.007 g, 48%) as a solid. 1H NMR (300 MHz, CDCl3): δ 7.87 (d, 2H, J=9.1 Hz), 6.61 (s, 1H), 6.43 (d, 2H, J=8.9 Hz), 4.32 (heptet, 1H, J=6.5 Hz), 4.18 (s, 2H), 3.83 (s, 1H), 2.19 (s, 3H), 1.52 (s, 9H), 1.32-1.28 (m, 9H), 0.99 (d, 3H, J=6.6 Hz).

Provenance & Evidence