Ethyl Acetate → 2-(Hydroxymethyl)-6-methylpyridine-4-carbonitrile

Participants

Reaction Steps

To a stirring solution of 1.20 g of (4-cyano-6-methylpyridin-2-yl)methyl 2,2,2-trifluoroacetate in 7 mL of THF was added 7% NaHCO3 (aqueous) solution to pH=8. The mixture was stirred at r.t. for 18 h, and EtOAc was added. The aqueous layer was extracted with EtOAc, and the combined extracts were washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (1 to 6) % MeOH/CHCl3 provided 535 mg of 2-(hydroxymethyl)-6-methylisonicotinonitrile in 73% yield.

Provenance & Evidence