Sodium borohydride → 1-(3-Chloropyridin-2-yl)ethanol

Participants

Reaction Steps

To a stirred solution of 0.20 g (1.2 mmol) of 1-(3-chloropyridin-2-yl)ethanone in 5 mL of methanol was added 0.072 g (1.9 mmol) of sodium borohydride and the resulting solution was stirred with gradual warming to ambient temperature over 1 h. The reaction mixture was carefully quenched with water and then all volatiles were removed in vacuo. The remaining aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulfate, filtered and evaporated to dryness in vacuo. The residue was purified by silica gel chromatography eluting with a 0-100% ethyl acetate in hexanes gradient to afford the title compound as a colorless gum (0.15 g, 75% yield). LC-MS: m/z (ES) 158.2 (MH)+.

Provenance & Evidence