Sulfuric Acid → 4-(2,6-Diethyl-4-methylphenyl)-2,6-dimethyl-5-(4-methylphenylsulfonyl)-2,3-dihydro-3-pyridazinone

Participants

Reaction Steps

To a 10 ml volume two-necked flask, 1-[2-(2,6-diethyl-4-methylphenyl)-1-methyl-2-oxoacetyl]-2-[1-(4-methylphenylsulfonyl)-2-propylidene]hydrazine ((4-36)-(1)-39) (809 mg), toluene (2.3 ml), and methanol (0.5 ml) were added. To the mixture, lithium hydroxide monohydrate (77 mg) was added at 0° C., stirred for 4 hours, and left to stand at 5° C. for 16 hours. The pH of the mixture was adjusted to 1 with 20 w/w % of sulfuric acid. The organic layer was removed, and then the aqueous layer was extracted with toluene 2 times. The organic layers were combined, washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography (hexane: ethyl acetate=3:1) to give 711 mg of 4-(2,6-diethyl-4-methylphenyl)-2,6-dimethyl-5-(4-methylphenylsulfonyl)-2,3-dihydro-3-pyridazinone ((2-36)-(1)-39).

Provenance & Evidence