Methane → 2-Cyclohexyl-1,2-dihydro-1,5-dimethyl-3H-pyrazol-3-one

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Reaction Steps

A mixture of 2-cyclohexyl-3-hydroxy-5-methylpyrazole (16.5 g) and dimethyl sulfate (10.9 g) was heated with stirring at 150°-160° for 6 hours and then allowed to cool to room temperature. A solution of sodium carbonate (6.5 g) in water (100 ml) was added, and the reaction mixture was heated at reflux temperature for 2 hours, cooled, and extracted with chloroform. The layer was dried and concentrated to give a dark oil, which was dissolved in methylene chloride, treated with charcoal and diatomaceous earth, filtered and concentrated. The concentrate was fractionally distilled, and the portion distilling at 118°/0.020 mm Hg was further purified by column chromatography on silica gel. Elution with chloroform-ethyl acetate (7:3), chloroform-ethyl acetate gradients, ethyl acetate, and ethanol afforded product from the ethyl acetate-rich chloroform-ethyl acetate gradient fractions and the ethyl acetate and ethanol fractions as determined by thin-layer chromatography and nuclear magnetic resonance spectroscopy. Product-rich fractions which were shown by gas chromatography to be highly pure were combined and concentrated to give 2-cyclohexyl-1,5-dimethyl-1,2-dihydro-3H-pyrazol-3-one (3.0 g) as an oil. The assigned structure was confirmed by infrared and nuclear magnetic resonance spectral analysis.

Provenance & Evidence