Sodium hydride → (E)-3-(1H-Indol-7-yl)acrylonitrile

HRID 54526

반응식

HRID 54526 반응식
[H-].[Na+].[C:3]([CH2:5]P(=O)(OCC)OCC)#[N:4].[NH:14]1[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][C:21]=2[CH:23]=O)[CH:16]=[CH:15]1>O1CCCC1.C(OCC)(=O)C>[C:3](/[CH:5]=[CH:23]/[C:21]1[CH:20]=[CH:19][CH:18]=[C:17]2[C:22]=1[NH:14][CH:15]=[CH:16]2)#[N:4]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 2734629Indole-7-carboxaldehyde

생성물 1

HCID 19959103(E)-3-(1H-Indol-7-yl)acrylonitrile

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

Sodium hydride, 60% dispersion in mineral oil (0.10 g, 2.5 mmol) is added in portions over 10 minutes to a stirred solution of diethyl cyanomethylphosphonate (0.44 g, 2.5 mmol) in tetrahydrofuran (10 ml) cooled in ice. The mixture is stirred for 15 minutes then a solution of 7-indole carboxaldehyde (0.30 g, 2.1 mmol) in tetrahydrofuran (2 ml) is added dropwise. The mixture is stirred for 30 minutes, diluted with ethyl acetate, washed with water, dried and evaporated. The residue is chromatographed on silica in ethyl acetate-hexane (1:3) to give the product.

후처리

  1. temperaturecooled in ice
  2. stirringThe mixture is stirred for 30 minutes
  3. washwashed with water
  4. customdried
  5. customevaporated
  6. customThe residue is chromatographed on silica in ethyl acetate-hexane (1:3)
  7. customto give the product

출처 및 근거

ORD 기록
ord-28339c89712f412387a749f34ff15d9b
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05622969

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