Thionyl Chloride → 4-(5-Chloromethyl-2-methoxyphenoxy)methyl-2-(2-furyl)-5-methyl-1,3-oxazole

Participants

Reaction Steps

To a mixture of (3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxyphenyl)methanol (7.0 g) and toluene (150 mL) was added thionyl chloride (3.16 g), and the mixture was heated under reflux for 1 hr. The reaction mixture was concentrated and ethyl acetate was added to the residue. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate and concentrated to give 4-(5-chloromethyl-2-methoxyphenoxy)methyl-2-(2-furyl)-5-methyl-1,3-oxazole as pale-brown crystals (7.30 g, yield 99%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 115-116° C.

Provenance & Evidence