Potassium Iodide → 2-{1-[2-(4-benzyloxy-phenyl)-oxazol-4-ylmethyl]-1H-imidazol-2-yl}-ethanol

HRID 854694Notes

Reaction equation

HRID 854694 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]=[C:18]([CH2:20]Cl)[N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:22][CH2:23][CH2:24][C:25]1[NH:26][CH:27]=[CH:28][N:29]=1.[I-].[K+].[OH-].[Na+]>CC(O)(CC)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[O:16][CH:17]=[C:18]([CH2:20][N:26]3[CH:27]=[CH:28][N:29]=[C:25]3[CH2:24][CH2:23][OH:22])[N:19]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 150160802-(1H-imidazol-2-yl)ethan-1-olHCID 220098452-(4-Benzyloxy-phenyl)-4-chloromethyl-oxazole

Product 1

HCID 694248212-{1-[2-(4-benzyloxy-phenyl)-oxazol-4-ylmethyl]-1H-imidazol-2-yl}-ethanolYield 37.3%

Reagents, catalysts & solvents 1

HCID 64052-Methyl-2-butanolSolvent

Procedure

A mixture of 2.10 g (7.0 mmol) 2-(4-benzyloxy-phenyl)-4-chloromethyl-oxazole, 0.86 g (7.7 mmol) 2-(2-hydroxyethyl)-1H-imidazole, 1.28 g (7.7 mmol) potassium iodide and 0.31 g (7.7 mmol) sodium hydroxide in 30 ml 2-methyl-2-butanol was stirred under reflux over night. After evaporation, water was added and the residue extracted into ethyl acetate. The extract was dried, evaporated and purified on silica. Elution with ethyl acetate/methanolic ammonia 85:15 yielded 0.98 g (37%) 2-{1-[2-(4-benzyloxy-phenyl)-oxazol-4-ylmethyl]-1H-imidazol-2-yl}-ethanol as tan solid.

Workup

  1. temperatureunder reflux over night
  2. customAfter evaporation, water
  3. additionwas added
  4. extractionthe residue extracted into ethyl acetate
  5. customThe extract was dried
  6. customevaporated
  7. custompurified on silica
  8. washElution with ethyl acetate/methanolic ammonia 85:15

Sources & evidence

ORD record
ord-36d36814a0dd4aa886832c1ee62ee5d8
Source dataset
uspto-grants-2007_08
Patent number
US07259262B2

Reaction notes

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