Attempted Synthesis of a Model Compound Used in the Study of a Variant of the Paterno-Buchi Reaction
Zorbo, James M. (Jamie), 1978-
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2,3-Dimethyl-2-cyclopentenone was successfully alkylated using NaH, diethyl carbonate, and two different bromide electrophiles, namely allyl and cinnamyl bromide, to afford two different esters in good yields (59% and 71%). Decarboethoxylation was performed on the allyl ester using 10% KOH/MeOH followed by heating under argon gas to afford 5-allyl-2,3-dimethyl-2-cyclopentenone (50% yield). One-step reduction of the ketone to the methylene ended in failure. However, reduction of a model compound, 2- pentyl-2-cyclopentenone, to an alcohol using DIBAL-H proved to be successful and afforded 2-pentyl-2-cyclopentenol. The reduction of the model alcohol to the methylene ended in failure. The volatility of the methylene products to be formed was thought be a major cause for the difficulty associated with completing the reduction step of our synthetic scheme.