Sodium borohydride → [2-(Benzyloxy)-4,6-dimethylpyridin-3-yl]methanol

Participants

Reaction Steps

35 g×2 batches: To a 0° C. solution of 2-(benzyloxy)-4,6-dimethylpyridine-3-carbaldehyde (Cpd X, 35.0 g, 145 mmol) in CH3OH (1000 mL) was added NaBH4 (6.60 g, 174 mmol) in portions. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under vacuum and the residue was diluted with NaHCO3 (sat., aq.). After the bubbling had stopped, the aqueous solution was extracted with EtOAc (2×500 mL). The combined organic layers were dried over Na2SO4, concentrated under vacuum, and purified by column chromatography (petroleum ether/EtOAc) to give [2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methanol (Cpd Y, 43 g, 61%) as a colorless oil.

Provenance & Evidence