Ammonium Chloride → (2-Chloropyridin-4-yl)methanol

Participants

Reaction Conditions

Reaction Steps

Methyl 2-chloropyridine-4-carboxylate (2.50 g, 14.60 mmol) was dissolved in anhydrous THF (50 mL) and this solution was cooled to −78° C. under N2 atmosphere. Diisobutylaluminium hydride 1.0 M in hexanes (63.3 mL, 63.30 mmol) was added dropwise stabilizing the temperature between −50° C. and −70° C. The reaction mixture was stirred 1.5 h at −78° C. and allowed to stand at room temperature for 3 h. A solution of aqueous 10% NH4Cl was slowly added and the mixture was extracted with ethyl acetate (3×300 mL). The combined organic layers were washed with water (3×20 mL), brine (2×20 mL), dried over MgSO4, filtered and evaporated. (2-Chloropyridin-4-yl)methanol SLA 07152 was obtained as a yellow oil (1.97 g, 94% yield).

Provenance & Evidence