Sodium Methoxide → 5-Methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde

HRID 545364Notes

Reaction equation

HRID 545364 reaction equation
Br[C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:4]([CH3:18])[C:3]=1[CH:19]=[O:20].[CH3:21][O-:22].[Na+]>CO>[CH3:21][O:22][C:2]1[N:6]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]([F:17])([F:16])[F:15])[CH:8]=2)[N:4]([CH3:18])[C:3]=1[CH:19]=[O:20]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 866260315-Bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde

Product 1

HCID 866260325-Methoxy-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 1.00 g (2.9 mmol) of 5-bromo-3-methyl-2-(3-trifluoromethoxy-phenyl)-3H-imidazole-4-carbaldehyde in 25 ml of MeOH was treated with 3.20 ml (17.3 mmol) sodium methoxide-solution (5.4 molar in MeOH) and then stirred at reflux for 48 hours. After cooling down to RT, the solvent was evaporated, cold water and EtOAc were added and the mixture then extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (n-heptane/EtOAc 4:1 to 1:1) to give 0.926 g (quant.) of the title compound as light yellow solid. MS: 301.1 (MH+).

Workup

  1. temperatureat reflux for 48 hours
  2. customthe solvent was evaporated
  3. additioncold water and EtOAc were added
  4. extractionthe mixture then extracted twice with EtOAc
  5. washthe organic phases were washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash column chromatography (n-heptane/EtOAc 4:1 to 1:1)

Sources & evidence

ORD record
ord-0693f24a0d9041de860c5157de914cc1
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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