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Microwave-Promoted Synthesis of a Carbocyclic Curcuminoid: An Organic Chemistry Laboratory Experiment

A microwave-promoted synthesis of a carbocyclic curcuminoid has been developed for the undergraduate organic chemistry laboratory curriculum. The experiment features several teaching points: A novel Knoevenagel iminium-mediated condensation forms a highly conjugated, intensely colored natural product. Reaction occurs uniquely at the less acidic positions of the diketone owing to the formation of a boron enolate formed in situ. Green chemistry is demonstrated by the use of microwave irradiation for efficient reaction, minimal use of solvent, and rapid and convenient workup conditions. Students from multiple lab sections obtained the product in good yield and purity and submitted reports containing their results and conclusions.