Benzyl Alcohol → 4-(Benzyloxy)pyridine

Participants

Reaction Conditions

Reaction Steps

A flask is charged with NaH (60% dispersion in mineral oil, 0.72 g, 18.0 mmol) then suspended in DMF (30 mL) and cooled to 5° C. To this mixture is added benzyl alcohol (1.04 mL, 10.0 mmol) drop-wise. The mixture is stirred for 15 minutes then 4-chloropyridine-HCl (1.00 g, 6.67 mmol) is added in three portions over 5 min. The resulting mixture is stirred at 5° C. for 10 min then warmed to 60° C. and stirred for 1.5 h. The mixture is then cooled to 23° C., treated with water, and extracted with EtOAc. The combined organics are dried with MgSO4, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (SiO2, 5% EtOAc in hexanes to 50% EtOAc in hexanes) gives the title intermediate (1.10 g, 89%).

Provenance & Evidence