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

HRID 1188010Notes

Reaction equation

HRID 1188010 reaction equation
[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:11]2[CH:15]=[C:14]([CH2:16][O:17][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[N:13]=[CH:12]2)=[CH:6][CH:5]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[CH3:1][O:2][C:3](=[O:35])[C:4]1[CH:5]=[CH:6][C:7]([CH2:10][N:11]2[CH:15]=[C:14]([CH2:16][OH:17])[N:13]=[CH:12]2)=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 688246604-(4-tert-Butyldiphenylsilyloxymethylimidazol-1-yl-methyl)benzoic acid methyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 4-(4-tert-Butyldiphenylsilyloxymethylimidazol-1-yl-methyl)benzoic acid methyl ester (1.6 g, 3.3 mmol) and tetrabutylammonium fluoride 1M in THF (3.3 ml, 3.3 mmol) in THF (10 ml) was stirred under argon at room temperature for 2 h. Water (15 ml) was added, the mixture was extracted with AcOEt, the organic phase washed with water, brine and dried over MgSO4.

Workup

  1. extractionthe mixture was extracted with AcOEt
  2. washthe organic phase washed with water, brine
  3. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-63e06740059c40988bc63cae95632ffa
Source dataset
uspto-grants-2014_03
Patent number
US08673955B2

Reaction notes

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