3-Chloro-4-pyridinecarboxaldehyde → (3-Chloropyridin-4-yl)methanol

Participants

Reaction Steps

A suspension of 3-chloro-4-pyridinecarboxaldehyde (43.80g, 0.310mol) in ethanol (200 ml) was cooled in an ice bath and treated with powdered sodium borohydride (5.85 g, 0.155 mol) added in portions over approximately 2 min. The resulting solution was removed from the ice bath and stirred at ambient temperature. After 1 hr the solution was recooled in an ice bath and treated with acetone (22 ml) to decompose excess borohydride. The solution was again removed from the ice bath and stirred at ambient temperature. After 30 min the reaction solution was evaporated under vacuum to a viscous oil.

Provenance & Evidence