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

HRID 1842883Notes

Reaction equation

HRID 1842883 reaction equation
[H-].[Na+].[C:3](#[N:5])[CH3:4].[F:6][C:7]([F:14])([F:13])[C:8](OCC)=[O:9]>O1CCOCC1>[F:6][C:7]([F:14])([F:13])[C:8](=[O:9])[CH2:4][C:3]#[N:5]

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 9794Ethyl trifluoroacetateHCID 24758Sodium hydride

Product 1

HCID 138435404,4,4-Trifluoro-3-oxobutanenitrileYield 98.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
10 °C

Procedure

To a stirred suspension of 60% NaH (33.80 g, 1.408 mol, 2 eq.) in dioxane (700 mL) was added acetonitrile (44.3 mL, 0.845 mol, 1.2 eq.) at 0° C. over a period of 30 min followed by ethyl trifluoroacetate (83.70 mL, 0.704 mol, 1.0 eq.). The reaction mixture was slowly and carefully heated to 10° C. for 3 h. The dioxane was evaporated under reduced pressure and the pH was adjusted to ˜6 with 1N HCl and the mixture extracted with ether (200 mL×4), dried (MgSO4) and the solvent evaporated under vacuum to get 4,4,4-trifluoro-3-oxobutanenitrile (95 g, crude, brown oil).

Workup

  1. customThe dioxane was evaporated under reduced pressure
  2. extractionthe mixture extracted with ether (200 mL×4)
  3. dry with materialdried (MgSO4)
  4. customthe solvent evaporated under vacuum

Sources & evidence

ORD record
ord-436721f6ea4a4f9ebd172329330c7f44
Source dataset
uspto-grants-2015_02
Patent number
US08946204B2

Reaction notes

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