Sodium borohydride → (2-Methoxypyridin-3-yl)methanol

Participants

Reaction Steps

To a solution of 2-methoxy-pyridine-3-carbaldehyde (2.05 g, 14.9 mmol) in MeOH (70 mL) cooled to 0° C. was added sodium borohydride (670 mg, 17.7 mmol, 1.18 equiv.) as a solid in one portion. The reaction was allowed to slowly warm to room temperature and stirred for 2 h. Excess hydride was consumed by the addition of H2O and the reaction mixture was concentrated under reduced pressure. The residue was taken back up in EtOAc and washed with H2O. The aqueous phase was back extracted with EtOAc and the combine organic phase was washed with brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The crude residue was purified by flash silica gel chromatography using a 5% MeOH/DCM to provide, after concentration of the eluent, to give (2-methoxy-pyridin-3-yl)-methanol (1.65 g, 11.9 mmol, 81.3 %) as a white solid.

Provenance & Evidence