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

HRID 1534063Notes

Reaction equation

HRID 1534063 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:10])([CH3:9])[C:5](OC)=[O:6].[C:11](#[N:13])[CH3:12]>O1CCCC1.O>[C:4]([C:5]([CH2:12][C:11]#[N:13])=[O:6])([CH3:10])([CH3:9])[CH3:3]

Participants

6

Reactant 3

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 69027Methyl pivalate

Product 1

HCID 108871Pentanenitrile, 4,4-dimethyl-3-oxo-Yield 56%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 9.6 g of sodium hydride in 300 ml of tetrahydrofuran was stirred at 60° C. while a mixture of 23.2 g of methyl trimethylacetate and 8.2 g of acetonitrile was added in one portion. The reaction mixture was heated at reflux for five hours, and then cooled to room temperature and concentrated by evaporation of the solvent under reduced pressure. The product thus formed was dissolved in water and washed with dichloromethane. The aqueous layer was made acidic with 1N hydrochloric acid, and the acidic solution was extracted with fresh dichloromethane. The organic extracts were combined, washed with water, dried, and the solvent was removed by evaporation to give 14.0 g of cyanomethyl tert.-butyl ketone.

Workup

  1. additionwas added in one portion
  2. temperatureThe reaction mixture was heated
  3. temperatureat reflux for five hours
  4. concentrationconcentrated by evaporation of the solvent under reduced pressure
  5. customThe product thus formed
  6. washwashed with dichloromethane
  7. extractionthe acidic solution was extracted with fresh dichloromethane
  8. washwashed with water
  9. customdried
  10. customthe solvent was removed by evaporation

Sources & evidence

ORD record
ord-beda95e830404c168061c5d0a2086fc4
Source dataset
uspto-grants-1992_02
Patent number
US05086184

Reaction notes

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