Reaktion #47207

Reaktionsgleichung

ethyl trifluoroacetate

acetonitrile

LDA

→

4,4,4-trifluoro-3-oxobutanenitrile

Ausbeute 56.7%

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigequenched with ice water
2. 2
   EinengenThe reaction was concentrated under vacuum
3. 3
   Extraktionthe residue extracted with ethyl ether
4. 4
   Extraktionextracted with dichloromethane
5. 5
   ExtraktionThe aqueous solution was extracted with ethyl ether
6. 6
   Trocknenthe combined organic layers dried over anhydrous sodium sulfate
7. 7
   Sonstigethe solvent was removed under vacuum

Vorschrift

To a cooled (−78° C.) solution of LDA (2M, 15 g, 39 mmol) in anhydrous THF (50 mL) was added drop-wise a solution of ethyl trifluoroacetate (2.5 g, 18 mmol) and acetonitrile (1.4 g, 35 mmol) in 15 ml THF. The reaction was kept at −78° C. for 45 min, warmed up to room temperature over 1 hour period and quenched with ice water. The reaction was concentrated under vacuum, the residue extracted with ethyl ether, the pH brought to 1 with concentrated HCl, extracted with dichloromethane. The aqueous solution was extracted with ethyl ether, the combined organic layers dried over anhydrous sodium sulfate, and the solvent was removed under vacuum to afford 1.4 g of 4,4,4-trifluoro-3-oxobutanenitrile as a yellow oil, which was used as such in the next step.

Quelle