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

Participants

Reaction Steps

To a suspension of NaH (6.0 g of a 60% dispersion, 0.15 mol) in THF (100 ml) was added dropwise trifluoroacetic acid ethyl ester (14.2 g, 0.1 mol) and anhydrous MeCN (50 g, 0.12 mol) in THF (100 ml). The resulting mixture was refluxed overnight, and then cooled to RT. After removal of the volatiles in vacuo, the residue was diluted in EtOAc and aqueous 10% HCl. The organic layer was washed with H2O and brine, dried (MgSO4), filtered and concentrated to yield 15 g of crude 4,4,4-trifluoro-3-oxo-butyronitrile which was used for the next step reaction without further purification.

Provenance & Evidence