Sodium Chloride → 1-[5-(4-t-Butylphenyl)-4-hydroxy-1-methyl-1H-pyrazol-3-yl]ethanone

HRID 1881555Notes

Reaction equation

[CH3:1][NH:2][N:3]=[CH:4][C:5](=[O:7])[CH3:6].[C:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18](=O)[CH:19]=[O:20])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9].FC1C=C(C(NN)=O)C=CC=1C(OC)=O.[Cl-].[Na+]>C(O)(=O)C.O>[C:8]([C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:2]([CH3:1])[N:3]=[C:4]([C:5](=[O:7])[CH3:6])[C:19]=2[OH:20])=[CH:14][CH:13]=1)([CH3:11])([CH3:10])[CH3:9]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Oxopropanal methylhydrazone (46.375 mmol, 4.64 g) synthesized in Reference Synthetic Example 1 and (4-tert-butylphenyl)(oxo)acetaldehyde synthesized in Reference Synthetic Example 4 (46.375 mmol, 8.82 g) were dissolved in acetic acid (140 mL) and stirred at 100° C. for 2 hours. The reactor was cooled to room temperature, and after addition of water (100 mL) and saturated aqueous sodium chloride (50 mL), it was extracted with chloroform three times. The resulting organic layer was dried and filtered, and the solvent was evaporated. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1) to give the desired product as a yellow solid (5.79 g, yield 46%).

Workup

temperatureThe reactor was cooled to room temperature
extractionwas extracted with chloroform three times
customThe resulting organic layer was dried
filtrationfiltered
customthe solvent was evaporated
customThe residue was purified by silica gel column chromatography (n-hexane/ethyl acetate=4/1)

Sources & evidence

ORD record: ord-7026c5b40b254fad94f91dff883000d6
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08318796B2

Reaction notes

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