Water → 4-[2-(3-bromophenyl)-2-oxo-acetyl]-1H-pyrrole-2-carbonitrile

HRID 646263노트

반응식

HRID 646263 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[CH:11]=[C:12]([C:15]#[N:16])[NH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.S([O-])([O-])(=O)=[O:18].[Mg+2].C(=O)(O)[O-].[Na+].[O-][Mn](=O)(=O)=O.[K+].[OH2:34]>CC(C)=O.CCOC(C)=O.C(OCC)(=O)C.CCCCCC>[Br:1][C:2]1[CH:3]=[C:4]([C:8](=[O:18])[C:9]([C:10]2[CH:11]=[C:12]([C:15]#[N:16])[NH:13][CH:14]=2)=[O:34])[CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 5

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 516892Sodium BicarbonateHCID 686993714-(3-bromo-phenylethynyl)-1H-pyrrole-2-carbonitrile

생성물 1

HCID 587922704-[2-(3-bromophenyl)-2-oxo-acetyl]-1H-pyrrole-2-carbonitrile수율 84%

시약·촉매·용매 3

HCID 180Acetone용매HCID 8857Ethyl Acetate용매HCID 21226206Ethyl acetate hexane용매

실험 절차

A solution of 4-(3-bromo-phenylethynyl)-1H-pyrrole-2-carbonitrile (2.85 g, 10.52 mmol) in acetone was treated with a 45° C. solution of magnesium sulfate (1.90 g, 15.78 mmol) and sodium bicarbonate (0.53 g, 6.31 mmol) in water, immediately treated with KMnO4 (3.74 g, 23.67 mmol), stirred for 15 minutes (TLC (silica gel, 25% ethyl acetate/hexane) indicated complete clean conversion), diluted with EtOAc and washed with water until the washings were colorless. The organic phase was dried (MgSO4), filtered and evaporated. The resultant residue was crystallized to purity from warm ethyl acetate/hexane to afford 4-[2-(3-bromophenyl)-2-oxo-acetyl]-1H-pyrrole-2-carbonitrile as a yellow crystalline solid, 2.68 g, 84% yield.

후처리

  1. washwashed with water until the washings
  2. dry with materialThe organic phase was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe resultant residue was crystallized to purity
  6. temperaturefrom warm ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-e55ded96fe654b1892f5d05c1823adfc
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07705030B2

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