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

HRID 1881557Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

2-Oxopropanal ethylhydrazone (4.736 mmol, 540.6 mg) synthesized in Reference Synthetic Example 2 and (4-tert-butylphenyl)(oxo)acetaldehyde (4.736 mmol, 901.0 mg) synthesized in Reference Synthetic Example 4 were dissolved in acetic acid (20 mL) and stirred at 100° C. for about 3.5 hours. Then, the solvent was evaporated, and the residue was dried by means of a vacuum pump and purified by silica gel thin layer chromatography (n-hexane/AcOEt=1/2, 3/1 and 4/1) to give the desired product as an orange liquid (212 mg, yield 160).

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 thin layer chromatography (n-hexane/AcOEt=1/2, 3/1 and 4/1)

Sources & evidence

ORD record: ord-3059e8543e264919a535abee2bbce748
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318796B2

Reaction notes

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