Water → 2-[2-(4-Phenylbenzyloxy)phenyl]-3-(imidazol-1-yl)propene

HRID 868529

Reaktionsgleichung

Reaktionsgleichung von HRID 868529
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]([CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1)=[CH2:9].[H-].[Na+].[C:18]1([C:24]2[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.O>CN(C)C=O>[C:18]1([C:24]2[CH:25]=[CH:26][C:27]([CH2:28][O:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[C:8]([CH2:10][N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)=[CH2:9])=[CH:30][CH:31]=2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 154634-Phenylbenzyl chlorideHCID 24758Sodium hydrideHCID 140621702-(2-Hydroxyphenyl)-3-(imidazol-1-yl)-1-propene

Produkt 1

HCID 140621272-[2-(4-Phenylbenzyloxy)phenyl]-3-(imidazol-1-yl)propene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(2-Hydroxyphenyl)-3-(imidazol-1-yl)-1-propene (400 mg, 2.0 mmole) was dissolved in dimethylformamide (5 ml) and sodium hydride (60% dispersion in oil)(110 mg, 2.75 mmole) was added to the solution with stirring and ice-cooling. After stirring for additional 30 minutes, 4-phenylbenzylchloride (490 mg, 2.42 mmole) was added and the mixture was stirred overnight at room temperature. Then, the mixture was poured into water (50 ml) and extracted with diethyl ether (75 ml×2). The extract was washed with water (50 ml×2) and dried over anhydrous sodium sulfate. After distilling off the solvent, the residue was subjected to chromatography on a silica gel column and eluted with methylene chloride/methanol to obtain the title compound (0.41 g, 55.9%), m.p. 90°-92° C. (recrystallized from ethyl acetate/n-hexane).

Aufarbeitung

  1. temperatureice-cooling
  2. stirringAfter stirring for additional 30 minutes
  3. stirringthe mixture was stirred overnight at room temperature
  4. extractionextracted with diethyl ether (75 ml×2)
  5. washThe extract was washed with water (50 ml×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationAfter distilling off the solvent
  8. washeluted with methylene chloride/methanol
  9. customto obtain
  10. customthe title compound (0.41 g, 55.9%), m.p. 90°-92° C. (recrystallized from ethyl acetate/n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6beb5f2a435d4e22a829fe488828d8e7
Quelldatensatz
uspto-grants-1988_10
Patentnummer
US04780471

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