Methanol → ethoxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetic acid

関与物質

反応条件

反応手順

A solution of ethyl hydroxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetate (8b) (20 mg, 0.055 mmol) and potassium hydroxide (50 mg, 0.89 mmol) in a mixture of water (2 mL), tetrahydrofuran (2 mL) and methanol (0.5 mL) was stirred at 60° C. for 12 hours. Water (10 mL) was added to the reaction mixture which was washed with diethyl ether (10 mL). The aqueous layer was acidified to pH 2 with an aqueous solution of hydrochloric acid 0.5N and extracted with dichloromethane. The organic layer was washed with brine (10 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by preparative TLC (dichloromethane/ethanol) to afford unexpected ethoxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetic acid (example 8) (5.3 mg, 0.017 mmol, 31%).

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