Ethanol → alpha-Methyl-3-pyridinemethanol

Participants

Reaction Steps

Sodium borohydride (1.75 g) was added in portions to a stirred solution of acetylpyridine (12.1 g) in ethanol (100 mL) at 0° C. The mixture was allowed to warm to room temperature and stirred for 20 min, then concentrated under reduced pressure to remove ethanol. The thick residue was diluted with 300 mL of dichloromethane, 25 mL of water and 5 mL of 20% NaOH. The aqueous layer was saturated with sodium chloride, and extracted with ethyl acetate (4×150 mL). The combined organic extracts were dried (MgSO4) and concentrated. Evaporative distillation of the crude oily product (14.0 g) at 1 mm, oven temperature 85°-95° C. gave 11.4 g of 3-(1-hydroxyethyl)pyridine as a colorless oil.

Provenance & Evidence