Sodium hydride → 3-(1-Methyl-5-triphenylmethylaminopyrazol-4-yl)acrylonitrile

HRID 349538ノート

反応式

HRID 349538 の反応式
[H-].[Na+].C(OP([CH2:11][C:12]#[N:13])(=O)OCC)C.[CH3:14][N:15]1[C:19]([NH:20][C:21]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([CH:40]=O)[CH:17]=[N:16]1>O1CCCC1>[CH3:14][N:15]1[C:19]([NH:20][C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:18]([CH:40]=[CH:11][C:12]#[N:13])[CH:17]=[N:16]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 179619601-Methyl-5-triphenylmethylaminopyrazole-4-carbaldehyde

生成物 1

HCID 693317453-(1-Methyl-5-triphenylmethylaminopyrazol-4-yl)acrylonitrile収率 60.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of sodium hydride (55% dispersion in mineral oil, 26.2 g, 600 mmol) in tetrahydrofuran (1000 ml) was added diethyl(cyanomethyl)phosphonate (106.3 g, 600 mmol) under ice-cooling. The mixture was stirred under ice-cooling for 20 minutes. To the mixture was added 1-methyl-5-triphenylmethylaminopyrazole-4-carbaldehyde (197 g, 530 mmol), and the mixture was stirred for 2 hours. The reaction mixture was poured into ice-cold water. The mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with diethyl ether to give 3-(1-methyl-5-triphenylmethylaminopyrazol-4-yl)acrylonitrile (E, Z mixture, 126 g) as a solid.

後処理

  1. temperaturecooling
  2. temperaturecooling for 20 minutes
  3. stirringthe mixture was stirred for 2 hours
  4. additionThe reaction mixture was poured into ice-cold water
  5. extractionThe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with diethyl ether

出典と根拠

ORDレコード
ord-efdb7497533745a4a77875ee3583e194
出典データセット
uspto-grants-2007_02
特許番号
US07179801B2

反応ノート

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