Indole → 1H-Indole-1-acetonitrile

HRID 8120노트

반응식

HRID 8120 반응식
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].Br[CH2:13][C:14]#[N:15]>CN(C)C=O.C(OCC)(=O)C>[N:1]1([CH2:13][C:14]#[N:15])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

참가 물질

6

반응물 3

HCID 798IndoleHCID 11534BromoacetonitrileHCID 24758Sodium hydride

생성물 1

HCID 122309041H-Indole-1-acetonitrile수율 27.1%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A 0° C. solution of indole (7 g, 59.8 mmol) in 200 ml of dimethylformamide is treated with NaH (60% dispersion in mineral oil; 3.1 g, 77.7 mmol). After 20 minutes, bromoacetonitrile (4.2 ml, 59.8 mmol) is added, and the resulting mixture is allowed to slowly warm to ambient temperature and stir overnight. The reaction mixture is diluted with ethyl acetate (500 ml) and washed with H2O (3×200 ml). The organic layer is dried over Na2SO4 and concentrated in vacuo. The crude residue is purified by flash chromatography (SiO2; 5% then 20% ethyl acetate in hexanes) to give 2.53 g of indol-1-yl-acetonitrile (27%).

후처리

  1. washwashed with H2O (3×200 ml)
  2. dry with materialThe organic layer is dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude residue is purified by flash chromatography (SiO2

출처 및 근거

ORD 기록
ord-7a4c2b57e5d34d249997ab15f038576e
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07087635B2

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