Reaction #51600

Reaction equation

Cesium carbonate

ethyl 4,4,4-trifluoroacetoacetate

methyl tosylate

→

product

Yield 60.1%

Ethyl 3-methoxy-3-trifluoromethylacrylate

Yield 60.1%

Solvents

dimethylformamide

dimethylformamide

Conditions

Workup

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

Procedure

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.

Source