Acetonitrile → Pentanenitrile, 4,4-dimethyl-3-oxo-

HRID 469761Notes

Reaction equation

HRID 469761 reaction equation
[H-].[Na+].C(O[C:6](=[O:11])[C:7]([CH3:10])([CH3:9])[CH3:8])C.[C:12](#[N:14])[CH3:13]>C1CCCCC1.O>[CH3:10][C:7]([CH3:8])([CH3:9])[C:6](=[O:11])[CH2:13][C:12]#[N:14]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 19838Ethyl pivalateHCID 24758Sodium hydride

Product 1

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8078CyclohexaneSolvent2×

Conditions

Temperature
80 °C

Procedure

To a refluxed solution of sodium hydride (33.18 g, 553.03 mmol) in 275 mL of cyclohexane is added a mixture of 2,2-dimethyl-propionic acid ethyl ester (30 g, 230.43 mmol) in 79 mL acetonitrile (553.03 mmol) in 25 mL of cyclohexane. The mixture is maintained at 80° C. overnight. The mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate. The combined organics are washed with water, dried over sodium sulfate, filtered and concentrated to afford title compound which was used crude in subsequent reaction. ESI m/z 124=MH−

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. washThe combined organics are washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-e8b26003bc5646c5b4af385d203010fc
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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