Trifluoroacetic acid → Diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate

HRID 1090817

반응식

HRID 1090817 반응식
[C:1]([C:9]1[NH:13][C:12]([C:14](OC(=O)C)([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([C:9]1[NH:13][C:12]([CH:14]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:11][CH:10]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 6422Trifluoroacetic acid2회HCID 12052Triethylsilane2회HCID 54151482HCID 54151482, 화합물

생성물 1

HCID 9949366Diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate수율 50%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
40 °C

실험 절차

To a solution of diethyl (5-benzoylpyrrol-2-yl)-acetoxymethanedicarboxylate (142 mg, 0.367 mmol) and triethylsilane (102 mg, 0.440 mmol) in methylene chloride (10 mL) was added trifluoroacetic acid (84 mg, 0.734 mmol). The reaction mixture was stirred at 40° C. for 24 hours. Additional triethyl silane (51 mg, 0.220 mmol) and trifluoroacetic acid (84 mg, 0.734 mmol) was added. The reaction mixture was stirred at 40° C. for an additional 24 hours. The mixture was cooled to room temperature, washed with cold 10% aqueous sodium hydroxide and saturated aqueous sodium chloride, and concentrated under reduced pressure. The residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (87:13) to provide 60 mg (50%) of diethyl (5-benzoylpyrrol-2-yl)methane-dicarboxylate.

후처리

  1. stirringThe reaction mixture was stirred at 40° C. for an additional 24 hours
  2. temperatureThe mixture was cooled to room temperature
  3. washwashed with cold 10% aqueous sodium hydroxide and saturated aqueous sodium chloride
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (87:13)

출처 및 근거

ORD 기록
ord-45462bd281c8487caa0b0a8ec0a9d15f
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082950

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