2-(4-(tert-Butyl)phenyl)-2-oxoacetaldehyde → [5-(4-t-butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl](phenyl)methanone

HRID 2103869Notes

Reaction equation

[CH3:1][NH:2][N:3]=[CH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23](=O)[CH:24]=[O:25])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]>C(O)(=O)C>[C:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:2]([CH3:1])[N:3]=[C:4]([C:5]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[O:12])[C:24]=2[OH:25])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 100 °C

Procedure

Oxo(phenyl)acetaldehyde methylhydrazone (5.46 mmol, 886 mg) synthesized in Reference Synthetic Example 36 and (4-t-butylphenyl)(oxo)acetaldehyde (5 mmol, 951 mg) were dissolved in acetic acid (26 mL) and stirred at 100° C. for about 2 hours. Then, the solvent was evaporated, and the residue was recrystallized from chloroform/n-hexane to give the desired product as a yellow solid (993 mg, yield 59%).

Workup

customThen, the solvent was evaporated
customthe residue was recrystallized from chloroform/n-hexane

Sources & evidence

ORD record: ord-79db79f0e7314e74bf8b77db0dda2ecc
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576115B2

Reaction notes

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