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) was cooled at 0° C. with an ice bath. NaBH4 (0.31 g, 8.14 mmol) was added in four portions under stirring. The mixture was stirred at 0° C. for 10 minutes, then allowed to warm at room temperature and stirred for additional 30 minutes. The reaction mixture was concentrated under vacuum and the residue was partitioned between Et2O and ice-cooled water. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and evaporated (5.05 g, 91% yield).

Provenance & Evidence