Sodium borohydride → Ethyl 2-hydroxy-2-(2-phenyl-1-benzothiophen-3-yl)acetate

Participants

Reaction Steps

Sodium borohydride (53 mg, 1.40 mmol) was added to a solution of ethyl 2-oxo-2-(2-phenyl-1-benzothiophen-3-yl)acetate (2b) (430 mg, 1.38 mmol) in a mixture of methanol (10 mL) and tetrahydrofuran (5 mL) under a nitrogen atmosphere. The reaction mixture was stirred for 1 hour, quenched with water (2 mL) and concentrated in vacuo. The residue was diluted with dichloromethane (20 mL), washed with water (2×10 mL), brine (10 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (dichloromethane/ethanol 99/1) to afford the desired alcohol (2c) as a white solid (190 mg, 0.60 mmol, 44%).

Provenance & Evidence