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

Participants

Reaction Steps

A solution of butyllithium (1.6 M, 3.75 mL, 6 mmol) was added at −20° C. to a solution of 3-phenyl-1-benzothiophene (3a) (1.18 g, 5.61 mmol) in tetrahydrofuran (20 mL) under a nitrogen atmosphere. After 1 hour, a solution of ethyl glyoxylate in toluene (50%, 1.2 mL, 6 mmol) was added. The reaction mixture was slowly warmed to room temperature for 2 hours, quenched with water (5 mL) and concentrated in vacuo. The residue was partitioned between dichloromethane (40 mL) and water (15 mL). The organic layer was washed with water (2×15 mL), brine (15 mL), dried over sodium sulfate, filtered and evaporated to dryness. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 90/10) to afford the desired alcohol (3b) as a white solid (340 mg, 1.09 mmol, 20%).

Provenance & Evidence