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

HRID 1881559Notes

Reaction equation

[CH2:1]([NH:8][N:9]=[CH:10][C:11](=[O:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24](=O)[CH:25]=[O:26])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]>C(O)(=O)C>[C:14]([C:18]1[CH:23]=[CH:22][C:21]([C:24]2[N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:9]=[C:10]([C:11](=[O:13])[CH3:12])[C:25]=2[OH:26])=[CH:20][CH:19]=1)([CH3:17])([CH3:16])[CH3:15]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Oxopropanal benzylhydrazone (2.314 mmol, 408 mg) synthesized in the same manner as in Reference Synthetic Examples 1 and 2 and (4-tert-butylphenyl)(oxo)acetaldehyde (1.929 mmol, 366.9 mg) synthesized in Reference Synthetic Example 4 were dissolved in acetic acid (9 mL) and stirred at 100° C. for about 6 hours. Then, the solvent was evaporated, and the residue was dried by means of a vacuum pump and purified by silica gel column chromatography (n-hexane/AcOEt=3/1, and 4/1) to give the desired product as a yellow solid (74.1 mg, yield 11%).

Workup

customsynthesized in Reference Synthetic Example 4
customThen, the solvent was evaporated
customthe residue was dried by means of a vacuum pump
custompurified by silica gel column chromatography (n-hexane/AcOEt=3/1, and 4/1)

Sources & evidence

ORD record: ord-43c5d407a3ea41a6a8e60824443363b5
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318796B2

Reaction notes

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