Reaktion #51600

Reaktionsgleichung

Cesium carbonate

ethyl 4,4,4-trifluoroacetoacetate

methyl tosylate

→

product

Ausbeute 60.1%

Ethyl 3-methoxy-3-trifluoromethylacrylate

Ausbeute 60.1%

Lösungsmittel

dimethylformamide

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

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