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

HRID 35574

反応式

HRID 35574 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒2 回HCID 962Water溶媒

反応条件

温度
0 °C

実験手順

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 water and then extracted with ethyl acetate. The extract was washed successively with water and brine, and then dried over magnesium 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).

後処理

  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 magnesium sulfate
  6. customRemoval of the solvent
  7. customgave an oil which
  8. distillationwas purified by distillation under reduced pressure

出典と根拠

ORDレコード
ord-92c75c2f96ad4384a5b901ce45dfdb1d
出典データセット
uspto-grants-1988_08
特許番号
US04767768

関連ノート

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