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

Temperature

70 °C

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.

1. additionwas added to the resulting reaction mixture within 40 minutes
2. temperatureThe mixture was heated for 3 hours
3. temperaturecooled to room temperature
4. extractionUpon dilution with water (800 ml) the reaction mixture was extracted with diethyl ether three times
5. washThe combined organic phases were washed with water
6. customdried
7. concentrationThe mixture was concentrated
8. distillationthe residue distilled under reduced pressure to 30

ORD record

ord-eaca2d8216554a348feec94380868876

Source dataset

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05851952