Acetone → 1-[2-(2,6-Diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine

Participants

Reaction Steps

To a 25 mL volume three-necked flask, 300 mg of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(phenylmethylidene)hydrazine ((40-a)-(14)-6), 1.9 ml of acetone, 386 mg of potassium carbonate and 152 mg of dimethyl sulfate were added under a nitrogen atmosphere, and the mixture was stirred at room temperature for 1.5 hours. Water was added to the reaction mixture and the resultant was extracted with ethyl acetate three times. The organic layers were combined and dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane:ethyl acetate=10:1) to give 261 mg of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(phenylmethylidene)hydrazine ((40-b)-(15)-5) and 28 mg of methyl 2-(2,6-diethyl-4-methylphenyl)-2-oxo-N-(phenylmethylidene)ethanehydrazonate (compound (x-1)).

Provenance & Evidence