Sodium hydride → HCID 19390157、化合物

HRID 1757264ノート

反応式

HRID 1757264 の反応式
[Br-].[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:3].[H-].[Na+].[S:29]1[CH:33]=[CH:32][C:31]([C:34]2[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=2)[CH:37]=O)=[CH:30]1>CN(C)C=O.O.C(O)(=O)C>[S:29]1[CH:33]=[CH:32][C:31]([C:34]2[CH:35]=[C:36](/[CH:37]=[CH:7]/[CH2:6][CH2:5][CH2:4][C:2]#[N:3])[CH:39]=[CH:40][CH:41]=2)=[CH:30]1

参加物

7

反応物 3

HCID 24758Sodium hydrideHCID 45475263-(Thiophen-3-yl)benzaldehydeHCID 11418829(4-Cyanobutyl)(triphenyl)phosphanium bromide

生成物 1

HCID 19390157HCID 19390157、化合物収率 95.8%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

44.6 g of 4-cyanobutyltriphenylphosphonium bromide is dissolved in 250 ml of dimethylformamide, 4.2 g of 60% oily sodium hydride is added under ice cooling and stirring, then mixture is stirred at that temperature for 30 minutes, 18 g of 3-(3-thienyl)benzaldehyde is added, and the mixture is stirred at room temperature for further 20 hours. The reaction solution is diluted with water, acetic acid is added for neutralization, and then the solvent is distilled off under reduced pressure. The residue is led to two liquid phases using a system of water and ethyl ether, the organic layer is taken, washed with saturated saline and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is purified by silica gel column chromatography [Wako gel C-100, 500 g; hexane/ethyl acetate=4/1] to obtain 23.2 g (E)-6-[3-(3-thienyl)phenyl]-5-hexenenitrile as colorless oil.

後処理

  1. stirringmixture is stirred at that temperature for 30 minutes
  2. stirringthe mixture is stirred at room temperature for further 20 hours
  3. additionis added for neutralization
  4. distillationthe solvent is distilled off under reduced pressure
  5. washwashed with saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent is distilled off under reduced pressure
  8. customThe residue is purified by silica gel column chromatography [Wako gel C-100, 500 g; hexane/ethyl acetate=4/1]

出典と根拠

ORDレコード
ord-be8a7ce2ba844e1e9ffcc3bd6bab0c25
出典データセット
uspto-grants-1995_08
特許番号
US05444084

反応ノート

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