Diethyl Ether → 1-Phenylcyclopentanecarbonitrile

HRID 2169148ノート

反応式

HRID 2169148 の反応式
[H-].[Na+].[C:3]1([CH2:9][C:10]#[N:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:13][CH2:14][CH2:15][CH2:16]Br.CCOCC>CS(C)=O>[C:3]1([C:9]2([C:10]#[N:11])[CH2:16][CH2:15][CH2:14][CH2:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 80561,4-DibromobutaneHCID 8794PhenylacetonitrileHCID 24758Sodium hydride

生成物 1

HCID 661681-Phenylcyclopentanecarbonitrile

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒2 回

実験手順

To a suspension of sodium hydride (60%, 18.8 g, 470.08 mmol) in dimethyl sulfoxide (125 mL) was added dropwise a mixture of phenyl acetonitrile (19-01) (25 g, 213.6 mmol) and 1,4-dibromo-butane (20) (25.5 mL, 213.67 mmol) dissolved in dimethyl sulfoxide:ether (300 mL, 1:1). The mixture was stirred at room temperature for 3 h. After completion of the reaction, it was quenched with 1N HCl. The mixture was extracted with ethyl acetate, the separated organic part was dried and concentrated to get a crude product which was purified using normal silica column using 3% ethyl acetate in hexane to of ford 1-phenyl-cyclopentanecarbonitrile (21-01) (34 g, 92.92%) as a yellow liquid.

後処理

  1. additionwas added dropwise
  2. customAfter completion of the reaction, it
  3. customwas quenched with 1N HCl
  4. extractionThe mixture was extracted with ethyl acetate
  5. customthe separated organic part was dried
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-d500b1f6f08b4da2b2aaef445fe96e7d
出典データセット
uspto-grants-2015_06
特許番号
US09045486B2

反応ノート

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