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

HRID 54526ノート

反応式

HRID 54526 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-28339c89712f412387a749f34ff15d9b
出典データセット
uspto-grants-1997_04
特許番号
US05622969

反応ノート

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