Pyrazole → 1-Phenyl-2-(1H-pyrazol-1-yl)ethanone

HRID 133474

Reaction equation

HRID 133474 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[NH:11]1[CH:15]=[CH:14][CH:13]=[N:12]1.C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O>[C:5]1([C:3](=[O:4])[CH2:2][N:11]2[CH:15]=[CH:14][CH:13]=[N:12]2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 1048PyrazoleHCID 107572-ChloroacetophenoneHCID 11430Potassium Carbonate

Product 1

HCID 27663751-Phenyl-2-(1H-pyrazol-1-yl)ethanone

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1.5 g (9.7 mmol) of 2-chloroacetophenone in 10 mL of MeCN, 0.7 g (10.3 mmol) of pyrazole was added. After all the solids dissolved, 1.4 g (10.1 mmol) of ground K2CO3 was added and the mixture was stirred for 5 h. The reaction was diluted with EtOAc, filtered, and the solid was washed with EtOAc. The filtrate was washed with water and brine, then was dried and concentrated. The residue was chromatographed on a flash column using a gradient of 10-50% EtOAc-hexane to isolate desired product.

Workup

  1. dissolutionAfter all the solids dissolved
  2. filtrationfiltered
  3. washthe solid was washed with EtOAc
  4. washThe filtrate was washed with water and brine
  5. customwas dried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on a flash column

Sources & evidence

ORD record
ord-1eabe1ca28e24df185018b6299bd77d2
Source dataset
uspto-grants-2008_06
Patent number
US07390835B2

Linked notes

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