Water → 1-(4-methylbenzenesulfonyl)-1H-pyrrole-3-carboxylic acid

HRID 1748650Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748650
C([O:5][C:6]([C:8]1[CH:12]=[CH:11][NH:10][CH:9]=1)=[O:7])(C)(C)C.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.O>O1CCCC1.[H-].[Na+]>[CH3:23][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:10]2[CH:11]=[CH:12][C:8]([C:6]([OH:5])=[O:7])=[CH:9]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 11171190tert-butyl 1H-pyrrole-3-carboxylate

Produkt 1

HCID 27246931-(4-methylbenzenesulfonyl)-1H-pyrrole-3-carboxylic acidAusbeute 74,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24758Sodium hydrideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Sodium hydride (60%; 1.02 mg) was added at 0° C. to a solution of 1H-pyrrole-3-carboxylic acid tert-butyl ester (3.57 g) in tetrahydrofuran (71 ml), stirred at room temperature, then p-toluenesulfonic acid chloride (4.47 g) the mixture was stirred all night and all day. Water was added to the reaction solution, extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The organic solution was concentrated in vacuo, dichloromethane (30 ml) and trifluoroacetic acid (15 ml) were added to the resulting residue and stirred at room temperature for four hours. The solvent was evaporated, water was added to the resulting residue and the precipitated solid was washed with water to give 1-[(4-methylphenyl)sulfonyl]-1H-pyrrole-3-carboxylic acid (4.2 g) as a pale yellow solid.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe organic solution was concentrated in vacuo, dichloromethane (30 ml) and trifluoroacetic acid (15 ml)
  5. additionwere added to the resulting residue
  6. stirringstirred at room temperature for four hours
  7. customThe solvent was evaporated
  8. additionwater was added to the resulting residue
  9. washthe precipitated solid was washed with water

Quellen und Nachweise

ORD-Eintrag
ord-9f6fd9551b4444a4bb6b0980a041c598
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150555B2

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