Water → 3-Phenyl-1-(p-toluenesulfonyl)indole-2-carboxylic acid

HRID 1871819ノート

反応式

HRID 1871819 の反応式
[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)(=[O:18])=[O:17])[C:8]=2[C:26]([O:28]C(C)(C)C)=[O:27])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC(Cl)(Cl)C(O)=O.O>C(Cl)Cl>[C:1]1([C:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[N:9]([S:16]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)(=[O:18])=[O:17])[C:8]=2[C:26]([OH:28])=[O:27])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 962WaterHCID 6421Trichloroacetic AcidHCID 18688802t-Butyl 3-phenyl-1-(p-toluenesulfonyl)indole-2-carboxylate

生成物 1

HCID 186887843-Phenyl-1-(p-toluenesulfonyl)indole-2-carboxylic acid収率 94.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 2.55 g of compound J in 10 cc of methylene chloride was added 2.20 g of trichloroacetic acid under ice-cooling and the mixture was stirred for 16 hours. Water was added to the reaction mixture, the desired compound was extracted with ethyl acetate. The extract was dried over magnesium sulfate and distilled to remove the solvent. The crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=3/7) to obtain 2.10 g of 3-phenyl-1-(p-toluenesulfonyl)indole-2-carboxylic acid. Yield: 94.1%.

後処理

  1. temperaturecooling
  2. extractionthe desired compound was extracted with ethyl acetate
  3. dry with materialThe extract was dried over magnesium sulfate
  4. distillationdistilled
  5. customto remove the solvent
  6. customThe crude product thus obtained
  7. customwas purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=3/7)

出典と根拠

ORDレコード
ord-643a4ea2d1e04452ae4d653d69ee501a
出典データセット
uspto-grants-2000_08
特許番号
USRE036832

反応ノート

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