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

HRID 646263ノート

反応式

HRID 646263 の反応式
[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

参加物

9

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 8857Ethyl Acetate溶媒HCID 21226206Ethyl acetate hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e55ded96fe654b1892f5d05c1823adfc
出典データセット
uspto-grants-2010_04
特許番号
US07705030B2

反応ノート

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