Water → 4-(4-Hydroxymethylimidazol-1-ylmethyl)benzoic acid methyl ester

HRID 1188009Notes

Reaction equation

HRID 1188009 reaction equation
[Si]([O:18][CH2:19][C:20]1[N:21]=[CH:22][NH:23][CH:24]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.Br[CH2:26][C:27]1[CH:36]=[CH:35][C:30]([C:31]([O:33][CH3:34])=[O:32])=[CH:29][CH:28]=1.O>C1(C)C=CC=CC=1>[CH3:34][O:33][C:31](=[O:32])[C:30]1[CH:35]=[CH:36][C:27]([CH2:26][N:23]2[CH:24]=[C:20]([CH2:19][OH:18])[N:21]=[CH:22]2)=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 962WaterHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178455513HCID 178455513, compound

Product 1

HCID 121126144-(4-Hydroxymethylimidazol-1-ylmethyl)benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-(tert-butyldiphenylsilyloxymethyl)-1H-imidazole (9.25 g, 27.4 mmol), methyl 4-bromomethylbenzoate (6.297 g, 27.4 mmol) and TEA (2.782 ml, 27.4 mmol) in toluene (250 ml) was refluxed for 1.5 h. Water (500 ml) was added, the mixture was extracted with AcOEt, the organic phase washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the resulting oil was purified by flash chromatography on silica gel (CH2Cl2/MeOH: 100/0 to 98/2) to give:

Workup

  1. temperaturewas refluxed for 1.5 h
  2. extractionthe mixture was extracted with AcOEt
  3. washthe organic phase washed with brine
  4. dry with materialdried over MgSO4
  5. customThe solvent was removed under reduced pressure
  6. customthe resulting oil was purified by flash chromatography on silica gel (CH2Cl2/MeOH: 100/0 to 98/2)
  7. customto give

Sources & evidence

ORD record
ord-c7af6baacdad4735979d313c4da187e8
Source dataset
uspto-grants-2014_03
Patent number
US08673955B2

Reaction notes

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