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

HRID 1090814

반응식

HRID 1090814 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.[C:14]([O:22][CH2:23][CH3:24])(=[O:21])[CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:25]([O-:28])(=[O:27])[CH3:26].[Na+]>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]([CH2:26][C:25]([O:28][CH:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:14]([O:22][CH2:23][CH3:24])=[O:21])=[O:27])=[CH:12][CH:13]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 3

HCID 7761Diethyl MalonateHCID 24370Phenyl(1H-pyrrol-2-YL)methanoneHCID 517045Sodium Acetate

생성물 1

HCID 57231278Diethyl {[(5-benzoyl-1H-pyrrol-2-yl)acetyl]oxy}propanedioate수율 57%

시약·촉매·용매 3

HCID 12416832Manganese triacetate dihydrate촉매HCID 176Acetic Acid용매HCID 3283Diethyl Ether용매

반응 조건

온도
70 °C

실험 절차

A mixture of 2-benzoylpyrrole (855 mg, 5 mmol), diethyl malonate (800 mg, 5 mmol), manganese(III) acetate dihydrate (4560 mg, 15 mmol) and sodium acetate (820 mg, 10 mmol) in acetic acid (30 mL) was stirred at 70° C. under a nitrogen atmosphere. The reaction mixture was 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 eluting with hexane/ethyl acetate (70:30) to provide 1.00 g (57%) of diethyl (5-benzoylpyrrol-2-yl)acetoxy-methanedicarboxylate.

후처리

  1. filtrationfiltered
  2. washThe filtrate was washed with 10% aqueous sodium hydroxide and saturated aqueous sodium chloride
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica eluting with hexane/ethyl acetate (70:30)

출처 및 근거

ORD 기록
ord-5c72ba68032442c5a009dccd10bf06b8
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05082950

연결된 노트

불러오는 중…