Imidazole → 3-(1-Imidazolyl)-benzaldehyde dimethyl acetal

HRID 1740434ノート

反応式

HRID 1740434 の反応式
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[CH3:8][O:9][CH:10]([O:18][CH3:19])[C:11]1[CH:16]=[CH:15][CH:14]=[C:13](Br)[CH:12]=1>CN(C)C=O.O.[Cu]>[CH3:19][O:18][CH:10]([O:9][CH3:8])[C:11]1[CH:12]=[CH:13][CH:14]=[C:15]([N:1]2[CH:5]=[CH:4][N:3]=[CH:2]2)[CH:16]=1

参加物

7

反応物 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 1053951-Bromo-3-(dimethoxymethyl)benzene

生成物 1

HCID 221178243-(1-Imidazolyl)-benzaldehyde dimethyl acetal収率 79.4%

試薬・触媒・溶媒 3

HCID 23978Copper触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
155 °C

実験手順

A solution of 296 mg of imidazole and 131 mg of sodium hydride (80% dispersion in mineral oil) in 2 ml of anhydrous dimethylformamide was stirred at room temperature for 1 hour under nitrogen. 1.0 g of 3-bromobenzaldehyde dimethyl acetal and 30 mg copper powder were then added and the mixture was stirred at 150-160° C. under nitrogen for 36 hours. The cooled mixture was diluted with 20 ml of water and extracted with four 25 ml portions of dichloromethane. The combined extracts were washed with two 25 ml portions of 25% aqueous ammonia, followed by two 25 ml portions of brine and then dried over anhydrous magnesium sulphate. The solution was concentrated under reduced pressure to give 0.75 g of 3-(1-imidazolyl)-benzaldehyde dimethyl acetal as a clear viscous oil.

後処理

  1. extractionextracted with four 25 ml portions of dichloromethane
  2. washThe combined extracts were washed with two 25 ml portions of 25% aqueous ammonia
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationThe solution was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-b8d2021883814275bd64abc29882abf0
出典データセット
uspto-grants-1999_10
特許番号
US05969139

反応ノート

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