Reaktion #718814

Reaktionsgleichung

sodium hydride

ethyl 2,2,3,3,3-pentafluoropropanoate

acetonitrile

→

4,4,5,5,5-pentafluoro-3-oxopentanenitrile

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONTo this was added
2. 2
   Temperaturdropwise, and the resulting colorless suspension was heated at 50° C. for 4 h
3. 3
   TemperaturAfter cooling to rt the reaction mixture
4. 4
   Einengenwas concentrated under reduced pressure
5. 5
   workup.ADDITIONthe residue poured into water (100 mL)
6. 6
   Extraktionextracted with diethyl ether (100 mL)
7. 7
   SonstigeThe aqueous layer was separated
8. 8
   Extraktionextracted with diethyl ether (2×200 mL)
9. 9
   TrocknenThe combined diethyl ether layers were dried over magnesium sulfate
10. 10
    Einengenthen concentrated under reduced pressure

Vorschrift

A stirred suspension of sodium hydride (15.6 g of a 60% dispersion in mineral oil, 0.39 mol) in THF (100 mL) was heated to 50° C. To this was added a mixture of ethyl 2,2,3,3,3-pentafluoropropanoate (25 g, 0.13 mol) and dry acetonitrile (5.3 g, 0.13 mol), dropwise, and the resulting colorless suspension was heated at 50° C. for 4 h. After cooling to rt the reaction mixture was concentrated under reduced pressure and the residue poured into water (100 mL) and extracted with diethyl ether (100 mL). The aqueous layer was separated, acidified to pH 2 with aqueous 2 M HCl and extracted with diethyl ether (2×200 mL). The combined diethyl ether layers were dried over magnesium sulfate then concentrated under reduced pressure to afford 4,4,5,5,5-pentafluoro-3-oxopentanenitrile an orange oil (17 g) which was used in the next step without further purification.

Quelle