Benzyl Alcohol → 2-(Benzyloxy)-4-methylpyridine

Participants

Reaction Steps

Sodium hydride (60% paraffin dispersion, 5.0 g, 120 mmol) was washed with hexane (5 mL) twice, and suspended in tetrahydrofuran (200 mL). To this suspension was added dropwise a solution of benzyl alcohol (14 g, 120 mol) in tetrahydrofuran (50 mL) at 0° C., and the mixture was allowed to warm to room temperature and stirred for 15 minutes. To this solution was added a solution of 2-bromo-4-methylpyridine (20 mL, 110 mol) in tetrahydrofuran (50 mL), and the mixture was heated to reflux for 14 hours. Water (200 mL) was added to the reaction mixture, and extracted with ethyl acetate. The extracted solution was dried, and the solvent was distilled off. The crude product was distilled under reduced pressure to obtain a title compound (13 g, yield 67%).

Provenance & Evidence