An Indirect Method for Effecting the Addition of Methylmalonate to 2-Methylcyclohex-2-enone

References

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• The following results were obtained in Professor W. Dauben's laboratory. Equivalent amounts of the reactants with 1.5 equivalents of DBN in acetonitrile at 40 [ddot]C were kept for 40 h under 15 kbar. Compounds, 1a was obtained in 47% crude yield after flash chromatography. When the reaction was run at 48 h at 20 [ddot]C under 15 kbar, substantial amounts of 2a were recovered.
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• As expected attempts to methylate 1b directly led to a reverse Michael addition.
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• Infrared spectra were determined on a Beckman Acculab 4 infrared spectrophotometer using carbon tetrachloride solutions unless otherwise specified. Nuclear magnetic resonance spectra were determined on a Varian A-60 and T-60 NMR spectrometers using carbon tetrachloride solutions unless otherwise specified. Mass spectra were determined through the use of an AEI-MS 50 mass spectrometer at an ionization potential of 70 eV. Analyses were performed by Micro-Tech Laboratories Inc. All reactions were carried on in a nitrogen atmosphere unless otherwise specified. Boiling points and melting points are uncorrected.
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• The general procedure for work-up was addition of ether and water, followed by multiple extraction of the aqueous layer (saturated with sodium chloride in preparing 3a, 1a (part a)) with ether, and then washing with water and drying (MgSO4) the combined organic solutions.
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