Sodium hydride → (E,E)-4-ethyl-2,4-hexadienenitrile

HRID 868222

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HRID 868222 반응식
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[CH2:14](/[C:16](=[CH:19]\[CH3:20])/[CH:17]=O)[CH3:15]>C1C=CC=CC=1.O>[CH2:19](/[C:16](=[CH:14]\[CH3:15])/[CH:17]=[CH:5]/[C:3]#[N:4])[CH3:20]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 53628972-Butenal, 2-ethyl-

생성물 1

HCID 14329794(E,E)-4-ethyl-2,4-hexadienenitrile수율 41%

시약·촉매·용매 2

HCID 241Benzene용매2회HCID 962Water용매

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온도
0 °C

실험 절차

To a mixture of sodium hydride (60% in oil, 7.5 g) and dry benzene (200 ml) was added dropwise diethyl cyanomethylphosphonate (30 g) with stirring at 0° C. under dry nitrogen atmosphere. After stirring for 60 minutes at room temperature, a solution of (E)-2-ethyl-2-butenal (16.6 g) in dry benzene was added thereto at 0° C. with stirring. The resulting mixture was allowed to stand at room temperature for 60 minutes and diluted with warm water and then extracted with ethyl acetate. The extract was washed successively with water and brine, and then dried over magnsium sulfate. Removal of the solvent gave an oil which was purified by distillation under reduced pressure to give (E,E)-4-ethyl-2,4-hexadienenitrile (8.4 g).

후처리

  1. stirringAfter stirring for 60 minutes at room temperature
  2. stirringat 0° C. with stirring
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed successively with water and brine
  5. dry with materialdried over magnsium sulfate
  6. customRemoval of the solvent
  7. customgave an oil which
  8. distillationwas purified by distillation under reduced pressure

출처 및 근거

ORD 기록
ord-8ada94b92c174088b3adf8ee6c97f373
출처 데이터셋
uspto-grants-1988_10
특허 번호
US04778804

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