Ethyl 6-chloronicotinate → (6-Chloropyridin-3-yl)methanol

Participants

Reaction Steps

To a solution of ethyl 6-chloronicotinate (25.8 g, 0.139 mol) in ethanol was added sodiumborohydride (10.5 g, 0.278 mol), followed by stirring under an atmosphere of nitrogen gas at room temperature. After 41 hours, the reaction mixture was concentrated and then the residue was diluted with a saturated aqueous ammonium chloride solution and ethyl acetate. The organic layer was washed with a saturated aqueous ammonium chloride solution, dried over anhydrous sodium sulfate and concentrated. The residue was subjected to silica gel column chromatography (elution solvent; hexane, hexane:ethyl acetate=4:1, 2:1, and 3:2), to give the title compound (11.7 g, 58%) as a pale yellow solid.

Provenance & Evidence