Citric Acid → 3-Benzyloxy-1-isopropyl-4-(4-methoxybenzoyl)-5-phenoxy-1H-pyrazole

HRID 2102263Notes

Reaction equation

HRID 2102263 reaction equation
[CH2:1]([O:8][C:9]1[C:13]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:12](Br)[N:11]([CH:25]([CH3:27])[CH3:26])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1([OH:34])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C)C(=O)C>[CH2:1]([O:8][C:9]1[C:13]([C:14](=[O:23])[C:15]2[CH:20]=[CH:19][C:18]([O:21][CH3:22])=[CH:17][CH:16]=2)=[C:12]([O:34][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:11]([CH:25]([CH3:27])[CH3:26])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 311Citric AcidHCID 996PhenolHCID 11430Potassium CarbonateHCID 230795293-Benzyloxy-5-bromo-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole

Product 1

HCID 231133743-Benzyloxy-1-isopropyl-4-(4-methoxybenzoyl)-5-phenoxy-1H-pyrazoleYield 54.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

3-Benzyloxy-5-bromo-1-isopropyl-4-(4-methoxybenzoyl)-1H-pyrazole (43 mg), phenol (14 mg) and potassium carbonate (21 mg) were suspended in N,N-dimethylacetoamide (5 mL) and the mixture was stirred under reflux for 2 hours. The mixture was allowed to cool to room temperature, then 10% citric acid aqueous solution was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was sequentially washed with a saturated sodium hydrogen carbonate and brine. After the solution was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The obtained residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give the title compound, (24 mg).

Workup

  1. temperatureunder reflux for 2 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was sequentially washed with a saturated sodium hydrogen carbonate and brine
  4. dry with materialAfter the solution was dried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-591d77abe2c24174993ace6b3c9bb3df
Source dataset
uspto-grants-2009_08
Patent number
US07576064B2

Reaction notes

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