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

HRID 868529
Notes
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Reaction equation

HRID 868529 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-6beb5f2a435d4e22a829fe488828d8e7
Source dataset
uspto-grants-1988_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04780471

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes