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Ethyl benzoylacetate → 1-(2-methyl-1-phenylpropan-2-yl)-3-phenyl-1H-pyrazol-5(4H)-one

HRID 244936
Notes
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Reaction equation

HRID 244936 reaction equation
[CH3:1][C:2]([NH:11][N:12]=C(C)C)([CH3:10])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O=[C:17]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:18][C:19]([O:21]CC)=O.C(=O)([O-])O.[Na+]>C(O)(=O)C.C(OCC)(=O)C>[CH3:10][C:2]([N:11]1[C:19](=[O:21])[CH2:18][C:17]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[N:12]1)([CH3:1])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 516892Sodium BicarbonateHCID 866974591-(2-Methyl-1-phenylpropan-2-yl)-2-(propan-2-ylidene)hydrazine

Product 1

HCID 866974581-(2-methyl-1-phenylpropan-2-yl)-3-phenyl-1H-pyrazol-5(4H)-oneYield 50.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent
HCID 8857
Ethyl Acetate
Solvent

Conditions

Temperature
100 °C

Procedure

500 mg (2.45 mmol) of 1-(2-methyl-1-phenylpropan-2-yl)-2-(propan-2-ylidene)hydrazine was dissolved in 3.0 mL of glacial acetic acid, mixed with 429 mg (2.23 mmol) of ethyl 3-oxo-3-phenylpropanoate and stirred at 100° C. for 4 hours. The reaction solution was cooled to room temperature, diluted with ethyl acetate, neutralized with saturated aqueous sodium hydrogen carbonate (100 ml) and extracted with ethyl acetate. The resulting organic layer was dried over anhydrous sodium sulfate and filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography using hexane-ethyl acetate (100:1 to 9:1) as the eluent to give 330 mg of the desired product as a pale orange solid.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. extractionextracted with ethyl acetate
  3. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3e74574aaa524983b53b69002256e7b7
Source dataset
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08658686B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes