Reacción #51600

Ecuación de reacción

Cesium carbonate

ethyl 4,4,4-trifluoroacetoacetate

methyl tosylate

→

product

Rendimiento 60.1%

Ethyl 3-methoxy-3-trifluoromethylacrylate

Rendimiento 60.1%

Disolventes

dimethylformamide

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added to the resulting reaction mixture within 40 minutes
2. 2
   TemperaturaThe mixture was heated for 3 hours
3. 3
   Temperaturacooled to room temperature
4. 4
   ExtracciónUpon dilution with water (800 ml) the reaction mixture was extracted with diethyl ether three times
5. 5
   LavadoThe combined organic phases were washed with water
6. 6
   Otrodried
7. 7
   ConcentraciónThe mixture was concentrated
8. 8
   workup.DISTILLATIONthe residue distilled under reduced pressure

Procedimiento

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 20° 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 yield the product as a clear liquid (48.5 g, 60%) with a boiling point of 62-70° C. at 12 mm.

Fuente