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

HRID 1696450Notes

Reaction equation

HRID 1696450 reaction equation
[H-].[Na+].C(O[C:6](=[O:11])[C:7]([F:10])([F:9])[F:8])C.[CH3:12][C:13]#[N:14]>C1COCC1>[F:10][C:7]([F:8])([F:9])[C:6](=[O:11])[CH2:12][C:13]#[N:14]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydride

Product 1

HCID 138435404,4,4-Trifluoro-3-oxobutanenitrileYield 109.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. temperatureThe resulting mixture was refluxed overnight
  2. customAfter removal of the volatiles in vacuo
  3. additionthe residue was diluted in EtOAc
  4. washThe organic layer was washed with H2O and brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-c64a2de47b764925afd02a6a101de29c
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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