Condensation of Diethyl Malonate with Methyl Vinyl Ketone
Ethoxide-catalyzed reaction of diethyl malonate with methyl vinyl ketone yields 1-carboxy-6-methylbicyclo-[3.3.1]non-6-ene-2,4-dione (VI) and, after hydrolysis, 1-methyl-2-acetyl-4-carboxycyclohexene-1 (XI). The separately prepared mono-Michael adduct (V) can be cyclized in very good yield to a mixture of 4-carboethoxycyclohexane-1,3-dione (II) and 3-ethoxy-6-carboethoxy-Δ2-cyclohexenone (XIII). © 1964, American Chemical Society. All rights reserved.
Spencer, TA; Newton, MD; Baldwin, SW
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