1,4-Dibromobutane → 1-(Pyridin-2-yl)cyclopentanecarbonitrile

HRID 2169460

반응식

HRID 2169460 반응식
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].Br[CH2:13][CH2:14][CH2:15][CH2:16]Br>CS(C)=O.C(OCC)(=O)C.CCCCCC>[N:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1([C:10]#[N:11])[CH2:16][CH2:15][CH2:14][CH2:13]1

참가 물질

6

반응물 3

HCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 75959Pyridine-2-acetonitrile

생성물 1

HCID 529881341-(Pyridin-2-yl)cyclopentanecarbonitrile수율 82.2%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 21226206Ethyl acetate hexane용매

실험 절차

To a suspension of sodium hydride (60%) (0.745 g, 18.644 mmol) in dimethyl sulfoxide (10 mL) was dropwise added a mixture of pyridin-2-yl-acetonitrile (429) (1 g, 8.475 mmol) and 1,4-dibromo-butane (1.831 g, 8.475 mmol) dissolved in dimethyl sulfoxide-ether (10 mL, 1:1) at 0° C. and the reaction mixture was stirred for 30 min at the same temperature and then stirred at room temperature for 4 h. After completion of the reaction (monitored by silica TLC, Rf=0.4, in 10% ethyl acetate/hexane) the mixture was quenched with HCl (1N, 10 mL). The reaction mixture was diluted water (20 mL) and extracted with ethyl acetate (2×50 mL) combined extracts were washed with water (20 mL) and brine (2×20 mL). The organic phase was thereafter dried and concentrated in vacuo to get a crude mass which was purified by combi-flash to get 1-pyridin-2-yl-cyclopentanecarbonitrile (430) (1.2 g, 82%) as a color less liquid.

후처리

  1. additionwas dropwise added
  2. stirringstirred at room temperature for 4 h
  3. customwas quenched with HCl (1N, 10 mL)
  4. extractionextracted with ethyl acetate (2×50 mL)
  5. washwere washed with water (20 mL) and brine (2×20 mL)
  6. customThe organic phase was thereafter dried
  7. concentrationconcentrated in vacuo
  8. customto get a crude mass which
  9. customwas purified by combi-flash

출처 및 근거

ORD 기록
ord-e5404661149d4fe5b2b4a21fa81d1035
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09045486B2

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