Imidazole → 3-(Imidazol-1-yl)-1-[2-(4-phenylbutyl)phenoxy]-2-propanol

HRID 743206Notes

Reaction equation

HRID 743206 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[C:6]1([CH2:12][CH2:13][CH2:14][CH2:15][C:16]2[CH:26]=[CH:25][CH:24]=[CH:23][C:17]=2[O:18][CH2:19][CH:20]2[CH2:22][O:21]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>C(#N)C>[N:1]1([CH2:22][CH:20]([OH:21])[CH2:19][O:18][C:17]2[CH:23]=[CH:24][CH:25]=[CH:26][C:16]=2[CH2:15][CH2:14][CH2:13][CH2:12][C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 104931782-[2-(4-Phenylbutyl)phenoxymethyl]oxirane

Product 1

HCID 194239523-(Imidazol-1-yl)-1-[2-(4-phenylbutyl)phenoxy]-2-propanolYield 82.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

940 mg of imidazole were added to a solution of 780 mg of 2-[2-(4-phenylbutyl)phenoxymethyl]oxirane [prepared as described in Example 1(a)] in 25 ml of acetonitrile, and the resulting mixture was heated under reflux for 24 hours. At the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure. The resulting residue was purified by column chromatography through silica gel, using a 20:1 by volume mixture of methylene chloride and methanol as the eluent, to give 798 mg (yield 82%) of the title compound as a pale yellow oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 24 hours
  3. distillationAt the end of this time, the reaction mixture was freed from the solvent by distillation under reduced pressure
  4. customThe resulting residue was purified by column chromatography through silica gel
  5. additionby volume mixture of methylene chloride and methanol as the eluent

Sources & evidence

ORD record
ord-8f9b8976c0804d67855e7f0e00a7aedc
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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