Water → 2-Cyano-5-hydroxymethylpyridine

Participants

Reaction Steps

6-Cyanonicotinic acid methyl ester (701 mg) was dissolved in a mixed solvent of methanol (1 ml) and tetrahydrofuran (7 ml) and sodium borohydride (197 mg) was added under ice-cooling. The mixture was directly heated to room temperature and stirred overnight. Water (20 ml) was added, and the mixture was extracted with ethyl acetate (once with 50 ml and once with 30 ml), washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified with column chromatography (Yamazen HI-FLASH™ COLUMN size 2 L, elution solvent: hexane/ethyl acetate) to give the title compound (264 mg).

Provenance & Evidence