Pyrazole → 2-Chloro-4-(1-pyrazolyl)methylphenyl 2,2-dimethylpropanoate

HRID 1418715ノート

反応式

HRID 1418715 の反応式
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[H-].[Na+].[H][H].[CH3:10][C:11]([CH3:25])([CH3:24])[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21]Br)=[CH:17][C:16]=1[Cl:23])=[O:13]>CN(C)C=O>[CH3:10][C:11]([CH3:25])([CH3:24])[C:12]([O:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:1]2[CH:5]=[CH:4][CH:3]=[N:2]2)=[CH:17][C:16]=1[Cl:23])=[O:13]

参加物

6

反応物 4

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 21833670HCID 21833670、化合物HCID 178418361HCID 178418361、化合物

生成物 1

HCID 545168712-Chloro-4-(1-pyrazolyl)methylphenyl 2,2-dimethylpropanoate収率 60.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
10 °C

実験手順

A mixture of 15.3 g of pyrazole, 89.9 g of sodium hydride (60% oil dispersion) and 200 ml of anhydrous N,N-dimethylformamide was stirred at 60° to 70° C. under a nitrogen atmosphere for 2 hours. After the evolution of hydrogen gas ceased, the mixture was cooled to 10° C. To this mixture was added dropwise an anhydrous N,N-di-methylformamide (300 ml) solution of 68 g of 4-bromomethyl-2-chlorophenyl 2,2-di-methylpropanoate at room temperature under stirring over 1 hour, and the mixture was stirred at 80° C. for 1 hour. After cooling, the mixture was poured into ice water, which was extracted with ethyl acetate. The organic layer was washed with saturated aqueous ammonium chloride solution and then saturated sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography, which afforded 39.5 g of 2-chloro-4-(1-pyrazolyl)methylphenyl 2,2-dimethylpropanoate as a colorless oil. Yield, 60%.

後処理

  1. stirringunder stirring over 1 hour
  2. stirringthe mixture was stirred at 80° C. for 1 hour
  3. temperatureAfter cooling
  4. extractionwas extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous ammonium chloride solution
  6. dry with materialsaturated sodium chloride solution, dried with anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-c8ffb1d80ce5436980ab07d396a81a0d
出典データセット
uspto-grants-1999_03
特許番号
US05883262

反応ノート

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