Reaction #7067

Reaction equation

methyl p-toluenesulfonate

ethyl 4,4,4-trifluoroacetoacetate

cesium carbonate

→

title compound

Yield 56.0%

4,4,4-Trifluoro-3-methoxy-but-2-enoic acid ethyl ester

Yield 56.0%

Solvents

DMF

H2O

DMF

Conditions

Workup

1. 1
   TemperatureAfter cooling to room temperature
2. 2
   Extractionextracted with Et2O (2×150 mL)
3. 3
   Washwashed with H2O and brine
4. 4
   Dryingdried (Na2SO4)
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Procedure

To a solution of ethyl 4,4,4-trifluoroacetoacetate (12 mL, 82 mmol) in DMF (80 mL) is added cesium carbonate (26.4 g, 82 mmol). The reaction mixture is heated to 70° C. A solution of methyl p-toluenesulfonate (13.5 mL, 90 mmol) in DMF (30 mL) is then added dropwise during 30 min and the reaction mixture is stirred for an additional 1 hr. After cooling to room temperature, the reaction mixture is diluted with H2O (150 mL) and extracted with Et2O (2×150 mL). The organic extracts are combined and washed with H2O and brine, then dried (Na2SO4), filtered and concentrated to afford the title compound (9.0 g, 56%) as an oil which is used without further purification.

Source