Ethanol → Ethyl 5-(pyrrol-1-yl)salicylate

HRID 228621Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 228621
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([N:11]2[CH:15]=[CH:14][CH:13]=[CH:12]2)=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].Cl.CN(C)[CH2:19][CH2:20]CN=C=N.O.ON1C2C=CC=CC=2N=N1.C(O)C>CN(C)C=O.O>[N:11]1([C:8]2[CH:7]=[C:3]([C:4]([O:6][CH2:19][CH3:20])=[O:5])[C:2]([OH:1])=[CH:10][CH:9]=2)[CH:15]=[CH:14][CH:13]=[CH:12]1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 8537522-Hydroxy-5-(1H-pyrrol-1-yl)benzoic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 21899179Dimethylaminopropyl carbodiimide hydrochloride

Produkt 1

HCID 23078344Ethyl 5-(pyrrol-1-yl)salicylateAusbeute 36,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Hydroxy-5-(pyrrol-1-yl)benzoic acid (406 mg), 1-ethyl-3-(3-dimethylaminopropylcarbodiimide hydrochloride (420 mg), 1-hydroxybenzotriazole hydrate (337 mg), and ethanol (2 ml) were dissolved in N,N-dimethylformamide to prepare a solution which was then stirred at room temperature overnight. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was then washed with water and was dried over anhydrous sodium sulfate. The solvent was removed therefrom by distillation under the reduced pressure, and the residue was purified by column chromatography using acetone-hexane to give ethyl 5-(pyrrol-1-yl)salicylate (170 mg, yield 20%).

Aufarbeitung

  1. customto prepare a solution which
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe ethyl acetate layer was then washed with water
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. customThe solvent was removed
  6. distillationby distillation under the reduced pressure
  7. customthe residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7a7da2a4a5a04de8a576ec69868d3f5c
Quelldatensatz
uspto-grants-2009_07
Patentnummer
US07560558B2

Notizen zur Reaktion

Wird geladen…