Ethyl isobutyrate → 32039-89-7

HRID 383448Notes

Reaction equation

HRID 383448 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-7e2b0394085b43ca8bb4bbbecb540d59
Source dataset
uspto-grants-2013_02
Patent number
US08367665B2

Reaction notes

Loading…