Water → Methyl 4-benzyloxy3-(pyrrol-1-yl)benzoate

HRID 399835Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 399835
[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=1[N:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1.CC(C)([O-])C.[K+].O>CN(C)C=O>[CH2:1]([O:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=1[N:20]1[CH:24]=[CH:23][CH:22]=[CH:21]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 7498Benzyl BromideHCID 18945287Methyl 4-hydroxy-3-(pyrrol-1-yl)benzoateHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 18945286Methyl 4-benzyloxy3-(pyrrol-1-yl)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Benzylbromide (2.9 ml) was added to the mixture of methyl 4-hydroxy-3-(pyrrol-1-yl)benzoate (5.0 g) and potassium t-butoxide (2.7 g) in N,N-dimethylformamide (40 ml) under ice-cooling and the mixture was stirred for 5 hours at ambient temperature. The reaction mixture was poured into water and extracted with ethyl acetate. The extract layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration. The residue was crystallized from the mixture of toluene and diisopropyl ether and collected by filtration to give methyl 4-benzyloxy3-(pyrrol-1-yl)benzoate (4.2 g).

Aufarbeitung

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by concentration
  6. customThe residue was crystallized from the mixture of toluene and diisopropyl ether
  7. filtrationcollected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-55428f9c45d94f418a9188ce580559bc
Quelldatensatz
uspto-grants-1998_10
Patentnummer
US05824691

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