Ethyl isobutyrate → 4-Methyl-3-oxo-2-phenylpentanenitrile

HRID 383448노트

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HRID 383448 반응식
[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]

참가 물질

5

반응물 3

HCID 7342Ethyl isobutyrateHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

생성물 1

HCID 112176864-Methyl-3-oxo-2-phenylpentanenitrile수율 19.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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%).

후처리

  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)]

출처 및 근거

ORD 기록
ord-7e2b0394085b43ca8bb4bbbecb540d59
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367665B2

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