Water → HCID 57831389、化合物

HRID 1927390ノート

反応式

HRID 1927390 の反応式
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[CH:26]=[CH:25][C:10]([CH2:11][CH:12]([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])=[CH:9][CH:8]=1)=[O:6].Br[CH2:28][CH2:29][C:30]1[CH:37]=[CH:36][C:33]([C:34]#[N:35])=[CH:32][CH:31]=1.O>CN(C=O)C>[C:34]([C:33]1[CH:36]=[CH:37][C:30]([CH2:29][CH2:28][C:12]([CH2:11][C:10]2[CH:9]=[CH:8][C:7]([C:5]([O:4][CH3:3])=[O:6])=[CH:26][CH:25]=2)([C:19]([O:21][CH2:22][CH:23]=[CH2:24])=[O:20])[C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])=[CH:31][CH:32]=1)#[N:35]

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 128865484-(2-Bromoethyl)benzonitrileHCID 57831347Diallyl [4-(methoxycarbonyl)benzyl]malonate

生成物 1

HCID 57831389HCID 57831389、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
0 °C

実験手順

6.70 g (0.17 mol) of sodium hydride are added in portions to a solution of 55.71 g (0.17 mol) of diallyl 2-(4-methoxycarbonylbenzyl)malonate in 34 ml of DMF at 0° C. The reaction solution is then allowed to reach room temperature and is stirred for 1 hour. The reaction solution is then cooled to 0° C. again, 42.98 g (0.20 mol) of 4-(2-bromoethyl)benzonitrile in 21 ml of DMF are added, and the mixture is stirred at this temperature for 30 min. The mixture is then stirred at room temperature overnight. Water is added dropwise to the reaction mixture, which is then extracted three times with ethyl acetate, and the combined organic phases are washed with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the solvent is concentrated to dryness in vacuo. The resulting crude product is purified by flash chromatography (mobile phase: petroleum ether/ethyl acetate 3:1; 3 kg of silica gel). 36 g (78 mmol, 46% of theory) of a colorless solid are obtained.

後処理

  1. customto reach room temperature
  2. stirringthe mixture is stirred at this temperature for 30 min
  3. stirringThe mixture is then stirred at room temperature overnight
  4. extractionis then extracted three times with ethyl acetate
  5. washthe combined organic phases are washed with saturated sodium chloride solution
  6. dry with materialdried over sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe solvent is concentrated to dryness in vacuo
  9. customThe resulting crude product is purified by flash chromatography (mobile phase: petroleum ether/ethyl acetate 3:1; 3 kg of silica gel)
  10. custom36 g (78 mmol, 46% of theory) of a colorless solid are obtained

出典と根拠

ORDレコード
ord-e331a480cfb04e96bc7b6f11dae37ebd
出典データセット
uspto-grants-2012_05
特許番号
US08183271B2

反応ノート

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