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

HRID 1871819Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1871819
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 186887843-Phenyl-1-(p-toluenesulfonyl)indole-2-carboxylic acidAusbeute 94,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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%.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-643a4ea2d1e04452ae4d653d69ee501a
Quelldatensatz
uspto-grants-2000_08
Patentnummer
USRE036832

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