Ethyl isobutyrate → 32039-89-7

HRID 241609Notes

Reaction equation

HRID 241609 reaction equation
[CH2:1]([C:8]#[N:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[C:12](OCC)(=[O:16])[CH:13]([CH3:15])[CH3:14]>C1COCC1>[CH3:14][CH:13]([CH3:15])[C:12](=[O:16])[CH:1]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]#[N:9]

Participants

5

Reactant 3

HCID 7342Ethyl isobutyrateHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

Product 1

HCID 1121768632039-89-7Yield 19.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Benzylcyanide (1500 mg, 12.8 mmol) was dissolved in 150 ml dry THF and cooled down to 0° C. The solution was stirred at that temperature while NaH (60% in mineral oil, 663 mg) was added slowly. After the addition was completed, the mixture was stirred at 0° C. for 30 min and then the ice bath was removed and stirring continued at RT for 120 min. Ethyl isobutyrate (1785 mg, 15.4 mmol) was added at once and the reaction mixture heated at 60° C. for 2 h. The THF was removed in vacuo and the residue was then poured into ice-water. HCl 6M was added with stirring until neutral pH was reached. The mixture was extracted with EtOAc, dried over MgSO4 and concentrated in vacuo. The compound was purified by flash chromatography [silica; n-heptane-EtOAc (9:1)] to afford 4-methyl-3-oxo-2-phenyl-pentanenitrile (460 mg, 19%).

Workup

  1. additionwas added slowly
  2. additionAfter the addition
  3. customthe ice bath was removed
  4. stirringstirring
  5. waitcontinued at RT for 120 min
  6. temperatureheated at 60° C. for 2 h
  7. customThe THF was removed in vacuo
  8. additionthe residue was then poured into ice-water. HCl 6M
  9. additionwas added
  10. stirringwith stirring until neutral pH
  11. extractionThe mixture was extracted with EtOAc
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated in vacuo
  14. customThe compound was purified by flash chromatography [silica; n-heptane-EtOAc (9:1)]

Sources & evidence

ORD record
ord-2d25907188f04aafad78a7f5592b983d
Source dataset
uspto-grants-2014_02
Patent number
US08653072B2

Reaction notes

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