Potassium Carbonate → 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

HRID 2076262Notes

Reaction equation

HRID 2076262 reaction equation
C(=O)([O-])[O-].[K+].[K+].F[C:8]1[CH:15]=[CH:14][C:11]([CH:12]=[O:13])=[CH:10][C:9]=1[O:16][CH3:17].[CH3:18][C:19]1[N:20]=[CH:21][NH:22][CH:23]=1>CN(C=O)C>[CH3:17][O:16][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:8]=1[N:22]1[CH:23]=[C:19]([CH3:18])[N:20]=[CH:21]1)[CH:12]=[O:13].[CH3:17][O:16][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:8]=1[N:20]1[C:19]([CH3:18])=[CH:23][N:22]=[CH:21]1)[CH:12]=[O:13]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27373584-Fluoro-3-methoxybenzaldehydeHCID 178418800HCID 178418800, compound

Product 2

HCID 272824453-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehydeHCID 86602463HCID 86602463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

Potassium carbonate (4.05 g) was added to a DMF (50 mL) solution of 4-fluoro-3-methoxybenzaldehyde (3.00 g) and 4-methylimidazole (3.307 g), and the reaction liquid was stirred overnight at 100° C. The resultant reaction mixture was concentrated under reduced pressure, followed by adding water and ethyl acetate to the residue to separate an organic layer. The organic layer was washed with saturated saline, dried with anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified using silica gel column chromatography (elution solvent: a hexane-ethyl acetate system) to provide 3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde (856 mg) and 3-methoxy-4-(5-methyl-1H-imidazol-1-yl)benzaldehyde (44 mg).

Workup

  1. customthe reaction liquid
  2. customThe resultant reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. additionby adding water and ethyl acetate to the residue
  5. customto separate an organic layer
  6. washThe organic layer was washed with saturated saline
  7. dry with materialdried with anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified
  10. washelution solvent

Sources & evidence

ORD record
ord-0379e012803e44758beae3de1fba4327
Source dataset
uspto-grants-2011_04
Patent number
US07923563B2

Reaction notes

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