Ethyl 2-thiopheneglyoxylate → Ethyl 2-hydroxy-2-(thiophen-2-yl)acetate

Participants

Reaction Steps

A solution of ethyl 2-oxo-2-(thiophen-2-yl)acetate (5.00 g, 27.1 mmol) in ethanol (50 mL) is cooled at 0° C. with an ice bath. NaBH4 (0.31 g, 8.14 mmol) is added in four portions under stirring. The mixture is stirred at 0° C. for 10 minutes, then allowed to warm at RT and stirred for additional 30 minutes. Reaction is concentrated under vacuum and the residue is partitioned between Et2O and ice-cooled water. The organic layer is separated, washed with water and brine, dried over Na2SO4, filtered and evaporated to give a colorless liquid (5.05 g, 91% yield).

Provenance & Evidence