Methyl p-toluenesulfonate → 3-Methoxy-4,4,4-trifluoro-2-butenoic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (132.8 g) was added to a mixture of ethyl 4,4,4-trifluoroacetoacetate (75.0 g) and dimethylformamide (400 ml). The reaction mixture was heated to 70° C. for 30 minutes. A mixture of methyl tosylate (83.4 g) and dimethylformamide (150 ml) was added to the resulting reaction mixture within 40 minutes. The mixture was heated for 3 hours and cooled to room temperature. Upon dilution with water (800 ml) the reaction mixture was extracted with diethyl ether three times. The combined organic phases were washed with water and dried. The mixture was concentrated and the residue distilled under reduced pressure to 30 yield the product as a clear liquid (48.5 g, 60%) with a boiling point of 62°-70° C. at 12 mm.

Provenance & Evidence