Water → ethyl hydroxy-(1-methyl-2-phenyl-1H-indol-3-yl)-acetate

Participants

Reaction Steps

At 0° C., sodium tetraborohydride (78 mg, 2 mmol) was added to a solution of ethyl (1-methyl-2-phenyl-1H-indol-3-yl)-oxo-acetate (8a) (630 mg, 2.05 mmol) in a mixture of tetrahydrofuran (10 mL) and methanol (15 mL). The mixture was stirred at room temperature for 2 hours and then hydrolyzed with water. Methanol and tetrahydrofuran were removed under reduced pressure and the residue was diluted with dichloromethane. The organic layer was washed with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified by flash chromatography on silica gel (dichloromethane) to afford the desired alcohol (8b) (440 mg, 1.42 mmol, 69%).

Provenance & Evidence