HCID 58964502, compound → HCID 178494485, compound

HRID 2069280Notes

Reaction equation

HRID 2069280 reaction equation
[CH3:1][O:2][CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[N:11]=[CH:12][N:13](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:14]=2)=[CH:6][CH:5]=1>C(O)(C(F)(F)F)=O>[CH3:1][O:2][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:11]=[CH:12][NH:13][CH:14]=2)=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 58964502HCID 58964502, compound

Product 1

HCID 178494485HCID 178494485, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 2.800 g of 4-(4-methoxymethyl-phenyl)-1-trityl-1H-imidazole in 50 ml of TFA is stirred at room temperature for 3 hours. The reaction mixture is concentrated, taken up into ethyl acetate and the organic phase washed with sat. NaHCO3-solution and brine and dried over Na2SO4. Evaporation of the solvent gives a residue which is purified by flash chromatography on silica (40-63 μm particle size) with dichloromethane/methanol 93:7, yielding 1.169 g of 4-(4-methoxymethyl-phenyl)-1H-imidazole as a beige powder. Rt=2.906 min by HPLC on a nucleosil C18HD column with acetonitril+0.05% TFA/water+0.05% TFA, 20/80 to 100/0 over 6 min, 1.0 ml/min solvent flow. MS (API-ES, pos. scan): e/m=189 (M+1).

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washthe organic phase washed with sat. NaHCO3-solution and brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation of the solvent
  5. customgives a residue which
  6. customis purified by flash chromatography on silica (40-63 μm particle size) with dichloromethane/methanol 93:7

Sources & evidence

ORD record
ord-89244ceb6c834bf09db107b7e0a2bb2d
Source dataset
uspto-grants-2012_10
Patent number
US08299085B2

Reaction notes

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