Boron Trichloride → 4-(4-Chlorophenyl)-2-oxazolemethanol

Participants

Reaction Steps

181 ml of a 1M solution of boron trichloride in dichloromethane was added dropwise to a stirred solution of 21.5 g (90.5 mmol) of 4-(4-chlorophenyl)-2-ethoxymethyl-oxazole in 100 ml of dichloromethane. The temperature of the mixture was held below 10° C. during the addition by cooling with ice. After completion of the addition the mixture was stirred at room temperature for 2 hours and then poured on to 500 ml of ice/water. The dichloromethane phase was separated and the aqueous phase was extracted with 100 ml of dichloromethane. The combined dichloromethane extracts were washed with saturated sodium hydrogen carbonate solution, dried over sodium sulphate, filtered and evaporated. Recrystallization of the residue from toluene yielded 15.7 g (83%) of 4-(4-chlorophenyl)-2-oxazolemethanol of melting point 68°-71.5° C.

Provenance & Evidence