Chloroacetonitrile → 5-tert-Butyl-2-(chloromethyl)-1,3-oxazole

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of chloroacetonitrile (40 mL) and boron trifluoride etherate (20 mL, 0.16 mmol) at 0° C. was added 1-diazo-3,3-dimethyl-2-butanone in chloroacetonitrile (40 mL) dropwise over a period of 20 minutes. After addition was complete, the mixture was stirred at 0° C. for one hour and then partitioned between saturated NaHCO3, solution (700 mL) and CH2Cl2 (500 mL). The aqueous solution was extracted with CH2Cl2 (500 mL) and the combined organic layers were washed with brine (400 mL) and dried over MgSO4. After filtration, the solution was concentrated and then distilled under vacuum using an oil bath temperature of 40° C. The 2-(chloromethyl)-5-t-butyloxazole (9.2 g, 44% overall from the acid chloride, C8H12ClNO, MS m/e 174 (M+H)+) was obtained as a light yellow oil.

Provenance & Evidence