Thionyl Chloride → 4-Chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine

Participants

Reaction Steps

To thionyl chloride (4 mL) was added [2-(5-methyl-2-phenyl-4-oxazolylmethoxy)-4-pyridyl]methanol (1.19 g) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was concentrated, and saturated aqueous sodium hydrogencarbonate was added to the residue. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated. The obtained residue was subjected to silica gel column chromatography to give crystals of 4-chloromethyl-2-(5-methyl-2-phenyl-4-oxazolylmethoxy)pyridine from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless needle crystals (0.68 g, 54%). melting point: 104-105° C.

Provenance & Evidence