Diethyl Ether → 1-Phenylcyclopentanecarbonitrile

HRID 2169148

반응식

HRID 2169148 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 661681-Phenylcyclopentanecarbonitrile

시약·촉매·용매 1

HCID 679Dimethyl Sulfoxide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d500b1f6f08b4da2b2aaef445fe96e7d
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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