Phenyl(1H-pyrrol-2-YL)methanone → Diethyl {[(5-benzoyl-1H-pyrrol-2-yl)acetyl]oxy}propanedioate

HRID 1090815

반응식

HRID 1090815 반응식
[C:1]([C:9]1[NH:10][CH:11]=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17]>C(O)(=O)C.C(OCC)C.O.O.C([O-])(=O)C.[Mn+3].C([O-])(=O)C.C([O-])(=O)C>[C:1]([C:9]1[NH:10][C:11]([CH2:15][C:16]([O:18][CH:15]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:17])=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 2

HCID 24370Phenyl(1H-pyrrol-2-YL)methanoneHCID 84182Diethyl chloromalonate

생성물 1

HCID 57231278Diethyl {[(5-benzoyl-1H-pyrrol-2-yl)acetyl]oxy}propanedioate수율 150.8%

시약·촉매·용매 3

HCID 12416832Manganese triacetate dihydrate촉매HCID 176Acetic Acid용매HCID 3283Diethyl Ether용매

반응 조건

온도
80 °C

실험 절차

A mixture of 2-benzoylpyrrole (855 mg, 5 mmol), diethyl chloromalonate (973 mg, 5 mmol) and manganese(III) acetate dihydrate (4560 mg, 15 mmol) in acetic acid (30 mL) was stirred at 80° C. for four hours. The reaction was cooled to room temperature, diluted with diethyl ether and filtered. The filtrate was washed with 10% aqueous sodium hydroxide and saturated aqueous sodium chloride, dried (Na2SO4), and concentrated under reduced pressure. The residue was purified by column chromatography on silica (70-30, hexanes-ethyl acetate) to provide 1.46 g (75%) of diethyl (5-benzoylpyrrol-2-yl)acetoxymethane-dicarboxylate.

후처리

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered
  3. washThe filtrate was washed with 10% aqueous sodium hydroxide and saturated aqueous sodium chloride
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica (70-30, hexanes-ethyl acetate)

출처 및 근거

ORD 기록
ord-6fe3de6c3e0c4fc6bcecd92559a6ef55
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082950

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