Tetrahydrofuran → (6-Chloro-pyridin-2-yl)-ethanol

Participants

Reaction Steps

A solution of (6-chloro-pyridin-2-yl)-acetic acid ethyl ester (1.8 g, 9.05 mmol) in dry tetrahydrofuran (25 mL) was cooled to 0° C. Borane-dimethylsulfide complex (4.35 mL, 45.25 mmol) was added dropwise and the reaction mixture warmed to room temperature before heating at reflux overnight. The mixture was cooled to room temperature and quenched into saturated ammonium chloride solution and extracted with ethyl acetate. The separated organic layer was washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated to give the crude product which was purified by column chromatography over silica gel (60-120 mesh) using 30% ethyl acetate in chloroform as eluent to afford (6-chloro-pyridin-2-yl)-ethanol (0.76 g, 54%) as a liquid.

Provenance & Evidence