Dimethylformamide → methyl 2-(2,6-diethyl-4-methylphenyl)-N-(2-methyl-1-propylidene)-2-oxoethanehydrazonate

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Reaction Steps

To a 50 mL volume three-necked flask, 5.0 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-2-(2-methyl-1-propylidene)hydrazine ((40-a)-(14)-4), 16 ml of DMF, 7.19 g of potassium carbonate and 2.13 ml of dimethyl sulfate were added and the mixture was stirred at room temperature for 2.5 hours. Water and toluene were added to the reaction mixture and the resultant was extracted. Further, aqueous layer was extracted with toluene two times. The organic layers were combined and washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resultant was subjected to column chromatography (hexane:ethyl acetate=6:1 to 2:1) to give 3.04 g of 1-[2-(2,6-diethyl-4-methylphenyl)-2-oxoacetyl]-1-methyl-2-(2-methyl-1-propylidene)hydrazine ((40-b)-(15)-4) and 0.74 g of methyl 2-(2,6-diethyl-4-methylphenyl)-N-(2-methyl-1-propylidene)-2-oxoethanehydrazonate (x-2).

Provenance & Evidence