Trichloroacetyl chloride → 2-(2-Trichloroacetylpyrrol-1-yl)malonic acid ethyl (-)-menthyl ester

HRID 256587

반응식

HRID 256587 반응식
[CH:1]1([CH3:24])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:9])[CH3:8])[CH:3]([O:10][C:11](=[O:23])[CH:12]([N:18]2[CH:22]=[CH:21][CH:20]=[CH:19]2)[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:2]1.[Cl:25][C:26]([Cl:31])([Cl:30])[C:27](Cl)=[O:28]>C(Cl)(Cl)Cl>[CH:1]1([CH3:24])[CH2:6][CH2:5][CH:4]([CH:7]([CH3:8])[CH3:9])[CH:3]([O:10][C:11](=[O:23])[CH:12]([N:18]2[CH:19]=[CH:20][CH:21]=[C:22]2[C:27](=[O:28])[C:26]([Cl:31])([Cl:30])[Cl:25])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH2:2]1

참가 물질

4

반응물 2

HCID 6420Trichloroacetyl chlorideHCID 538719252-(Pyrrol-1-yl)malonic acid ethyl (-)-menthyl ester

생성물 1

HCID 536822462-(2-Trichloroacetylpyrrol-1-yl)malonic acid ethyl (-)-menthyl ester수율 94.9%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 2-(pyrrol-1-yl)malonic acid ethyl (-)-menthyl ester (64.0 g) in chloroform (80 ml) was added trichloroacetyl chloride (69.0 g), and the resulting mixture was refluxed for 7 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in ethyl acetate. The solution was washed with 5% aqueous sodium carbonate solution and then with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was chromatographed on silica gel using n-hexane/ethyl acetate (50:1) as the eluent. Fractions containing the title compound were pooled and evaporated under reduced pressure to give the title compound (87.0 g, 94.9%) as a colorless oil.

후처리

  1. temperaturethe resulting mixture was refluxed for 7 hours
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washThe solution was washed with 5% aqueous sodium carbonate solution
  5. dry with materialwith saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed on silica gel
  8. additionFractions containing the title compound
  9. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-092fc3f815bd4e3e90d5e158a41ec604
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05258382

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