Water → 2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

HRID 2247619Notes

Reaction equation

HRID 2247619 reaction equation
[H-].C[O:3]CCO[Al+]OCCOC.[Na+].[H-].[F:15][C:16]1[CH:23]=[C:22]([N:24]2[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]2)[C:21]([O:30][CH3:31])=[CH:20][C:17]=1[C:18]#N.O.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[F:15][C:16]1[CH:23]=[C:22]([N:24]2[CH:28]=[C:27]([CH3:29])[N:26]=[CH:25]2)[C:21]([O:30][CH3:31])=[CH:20][C:17]=1[CH:18]=[O:3]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydrideHCID 66961248HCID 66961248, compound

Product 1

HCID 730140352-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzaldehyde

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium bis(2-methoxyethoxy)aluminum hydride (65% solution in toluene, 11.4 mL) was added dropwise to a suspension of 2-fluoro-5-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzonitrile (8.85 g) in THF (180 mL) in a nitrogen atmosphere at −15° C., and the reaction solution was stirred for 1 hour. Water was added to the reaction mixture, and the mixture was stirred at room temperature for 10 minutes. Then, a 5 N aqueous solution of sodium hydroxide and ethyl acetate were added to the mixture and the organic layer was partitioned. The resulting organic layer was made acidic with 5 N aqueous hydrochloric acid, and the mixture was stirred. Then, the mixture was neutralized with 5 N aqueous sodium hydroxide and the organic layer was partitioned. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate) to obtain 3.32 g of the title compound. Properties data of the compound are as follows.

Workup

  1. stirringthe mixture was stirred at room temperature for 10 minutes
  2. customthe organic layer was partitioned
  3. stirringthe mixture was stirred
  4. customthe organic layer was partitioned
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate)

Sources & evidence

ORD record
ord-f83656a34bda4b48963fd9fdf3ad160c
Source dataset
uspto-grants-2010_03
Patent number
US07687640B2

Reaction notes

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