Methyl iodide → 1-Methyl-5-phenylpyrazole

Participants

Reaction Steps

Sodium hydride (60% dispersion in mineral oil, 0.83 g, 20.8 mmol) is suspended in THF (45 ml) and stirred under a nitrogen atmosphere. 3-Phenyl pyrazole (2.5 g, 17.3 mmol dissolved in THF, 15 ml) is added slowly, stirred for 30 minutes then iodomethane (1.3 ml, 20.8 mmol) added and stirred for 3 hrs. The reaction is added to water and extracted twice with ethyl acetate. The combined organic extracts are ished with brine, dried over Na2SO4, filtered and concentrated. The crude product is purified by chromatography using a hexane-ethyl acetate gradient (100% hexane to 40% ethyl acetate in hexane) to elute the title compound. Obtained is a mixture of 1-methyl-3-phenyl-1H-pyrazole and 1-methyl-5-phenyl-1H-pyrazole (2.6 g, 95% yield).

Provenance & Evidence