Acetonitrile → 4,4,5,5,5-Pentafluoro-3-oxopentanenitrile

Temperature

50 °C

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.

1. additionTo this was added
2. temperaturedropwise, and the resulting colorless suspension was heated at 50° C. for 4 h
3. temperatureAfter cooling to rt the reaction mixture
4. concentrationwas concentrated under reduced pressure
5. additionthe residue poured into water (100 mL)
6. extractionextracted with diethyl ether (100 mL)
7. customThe aqueous layer was separated
8. extractionextracted with diethyl ether (2×200 mL)
9. dry with materialThe combined diethyl ether layers were dried over magnesium sulfate
10. concentrationthen concentrated under reduced pressure

ORD record

ord-8ce88405bda04467bc1e12054826b593

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09320739B2