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Potassium Carbonate → 2-(1-(4-[4-(benzyloxy)phenyl]butyl}-1H-imidazol-2-yl)-1-ethanol

HRID 2084378
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2084378
I[CH2:2][CH2:3][CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1.[OH:20][CH2:21][CH2:22][C:23]1[NH:24][CH:25]=[CH:26][N:27]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:13]([O:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][CH2:4][CH2:3][CH2:2][N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[CH2:22][CH2:21][OH:20])=[CH:7][CH:8]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 150160802-(1H-imidazol-2-yl)ethan-1-olHCID 22259342Benzyl 4-(4-iodobutyl)phenyl ether

Produkt 1

HCID 222593132-(1-(4-[4-(benzyloxy)phenyl]butyl}-1H-imidazol-2-yl)-1-ethanolAusbeute 80,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Benzyl 4-(4-iodobutyl)phenyl ether (14.29 g), 2-(2-hydroxyethyl)imidazole (13.1 g), and potassium carbonate (5.39 g) were stirred in DMF (390 ml)at 60° C. for 16 hours. After cooling, the insoluble matter was filtered off; the filtrate was concentrated under reduced pressure. The residue was dissolved in ethyl acetate and washed with water and saturated saline. Under reduced pressure, the solvent was distilled off; the residue was purified by column chromatography (eluent: ethyl acetate-methanol=19:1→9:1). The eluate was recrystallized from ethyl acetate-methanol to yield the titled compound (10.99 g) as colorless crystals.

Aufarbeitung

  1. temperatureAfter cooling
  2. filtrationthe insoluble matter was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. washwashed with water and saturated saline
  6. distillationUnder reduced pressure, the solvent was distilled off
  7. customthe residue was purified by column chromatography (eluent: ethyl acetate-methanol=19:1→9:1)
  8. customThe eluate was recrystallized from ethyl acetate-methanol

Quellen und Nachweise

ORD-Eintrag
ord-bef30653f713421196f68db0ec2654d5
Quelldatensatz
uspto-grants-2004_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06716863B2

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