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

HRID 1418715노트

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HRID 1418715 반응식
[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]

참가 물질

6

반응물 4

HCID 1048PyrazoleHCID 24758Sodium hydrideHCID 21833670HCID 21833670, 화합물HCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

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온도
10 °C

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-c8ffb1d80ce5436980ab07d396a81a0d
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05883262

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