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

HRID 1504275Notes

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

Participants

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 and 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

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

Sources & evidence

ORD record: ord-760b2caa2fec48d3be24d6c50b4440d1
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09212348B2

Reaction notes

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