Acetonitrile → 4,4,4-Trifluoro-3-oxobutanenitrile

A solution of ethyl trifluoroacetate (14.2 g, 0.1 mol) and anhydrous acetonitrile (5.0 g, 0.12 mol) in THF (100 mL) was added dropwise to a suspension of NaH (60%, 6.0 g, 0.15 mol) in THF (100 mL) at 80° C. The resulting mixture was heated to reflux overnight, and then cooled to RT. The reaction mixture was concentrated in vacuo and the residue was diluted with EtOAc and 10% aq HCl. The organic layer was washed with water and brine, dried (MgSO4) and concentrated in vacuo to yield crude 4,4,4-trifluoro-3-oxo-butyronitrile (15 g), which was used without further purification.

1. temperatureThe resulting mixture was heated
2. temperatureto reflux overnight
3. concentrationThe reaction mixture was concentrated in vacuo
4. additionthe residue was diluted with EtOAc and 10% aq HCl
5. washThe organic layer was washed with water and brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD record

ord-01492667b1d148c3abb69e678177bd5c

Source dataset

uspto-grants-2012_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08143293B2