2-Oxo-2-(4-(trifluoromethyl)phenyl)acetaldehyde → 1-[4-hydroxy-1-methyl-5-(4-trifluoromethylphenyl)-1H-pyrazol-3-yl]ethanone

HRID 1881565Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2-Oxopropanal methylhydrazone (8.540 mmol, 855 mg) synthesized in Reference Synthetic Example 1 and (4-trifluoromethylphenyl)(oxo)acetaldehyde (6.432 mmol, 1.3 g) synthesized in Reference Synthetic Example 7 were dissolved in acetic acid (30 mL) and stirred at 100° C. for about 5 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=2/1, and 4/1) to give the desired product as an orange solid (157.3 mg, yield 8.6%).

Workup

customsynthesized in Reference Synthetic Example 7
customThen, the solvent was evaporated
customthe residue was dried by means of a vacuum pump
custompurified by silica gel column chromatography (n-hexane/AcOEt=2/1, and 4/1)

Sources & evidence

ORD record: ord-33aa5fad2bf44cfbb3d6323a59d61754
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318796B2

Reaction notes

Loading…