1,2-Dibromoethane → 1-(Pyrazin-2-YL)cyclopropanecarbonitrile

HRID 931156ノート

反応式

HRID 931156 の反応式
[H-].[Na+].[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[CH2:9][C:10]#[N:11].Br[CH2:13][CH2:14]Br>CN(C)C=O>[N:3]1[CH:8]=[CH:7][N:6]=[CH:5][C:4]=1[C:9]1([C:10]#[N:11])[CH2:14][CH2:13]1

参加物

5

反応物 3

HCID 78391,2-DibromoethaneHCID 24758Sodium hydrideHCID 12782906(Pyrazin-2-yl)acetonitrile

生成物 1

HCID 584311071-(Pyrazin-2-YL)cyclopropanecarbonitrile収率 31.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

To a suspension of sodium hydride (0.386 g, 16.1 mmol) in anhydrous N,N-dimethylformamide (5 mL) was added dropwise a solution of 2-(pyrazin-2-yl)acetonitrile (0.55 g, 4.6 mmol) and 1,2-dibromoethane (2.25 g, 11.9 mmol) in anhydrous N,N-dimethylformamide (8 mL) over a period of 10 min at room temperature. The mixture was stirred for 18 h, then was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was purified via column chromatography (100-200 mesh silica gel, 100% dichloromethane) to afford 1-(pyrazin-2-yl)cyclopropanecarbonitrile (210 mg, 31%).

後処理

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude material was purified via column chromatography (100-200 mesh silica gel, 100% dichloromethane)

出典と根拠

ORDレコード
ord-035158bd72094f139941edfd772382ab
出典データセット
uspto-grants-2016_03
特許番号
US09296745B2

反応ノート

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