Sodium Chloride → (2-Chloropyridin-3-yl)methanol

Participants

Reaction Steps

A mixture of 2-chloronicotinic acid (5.0 g, 31.7 mmol) and thionyl chloride (20 mL) was heated at reflux for 1.5 h. The reaction mixture was concentrated in vacuo to remove an excess thionyl chloride. The resulting solid was added in portions to a solution of sodium borohydride (4.3 g, 114 mmol) in water at 10° C. The reaction was maintained at 10-15° C. during the addition to NaBH4. The reaction mixture was then warmed to room temperature. The mixture was saturated with NaCl and extracted with ether (30 mL×3). The combined organic layer was dried over MgSO4 and concentrated in vacuo to afford 4.1 g (90%) of (2-chloro-pyridin-3-yl)-methanol.

Provenance & Evidence