Pyridine → 2-Benzyl-4-(chloromethyl)furan

Participants

Reaction Conditions

Reaction Steps

A solution of 13 g of thionyl chloride in toluene was added dropwise over 15 minutes to a mixture of 15.8 g pyridine and 18.8 g 2-benzyl-4-hydroxymethylfuran, in toluene, at a temperature of 0°-5° C. The mixture was slowly warmed to 80° C. and stirred for 11/2 hours and then cooled in an ice-bath, poured into ice and filtered. The resulting solution was extracted with diethyl ether, washed with water and then with sodium bicarbonate solution, and dried over magnesium sulphate. The solution was then stripped of solvent, yielding a brown oil, which was chromatographed over silica gel using toluene as eluent to give 2-benzyl-4-chloromethylfuran (1A) as a brown oil.

Provenance & Evidence