Conjugate Addition-Decarboxylation of Magnesium Monoethyl Malonate to Enones: A Convenient One-Flask Addition of Acetate

References

• McMurry , J. E. and Musser , J. 1975 . J. Org. Chem. , 40 : 2556
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• Krapcho , A. P. and Lovey , A. J. 1973 . Tetrahedron Letters , : 957 The procedure of Krapcho is probably the best method for effecting decarbalkoxylation of diethylmalonate Michael adducts:
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• Bram , G. and Vilkas , M. 1964 . Bull. Soc. Chim. France , : 945 Magnesium monoethyl malonate is best prepared by the general procedure of, Magnesium turnings (2.43 g, 0.1 mol), ethanol (30 ml), and monoethyl malonate (13.21 g, 0.10 mol) are placed in a dry flask under nitrogen atmosphere. Several drops dibromoethane are added and an exothermic reaction commences. After 1 hr., the mixture is warmed to 70°, and when the reaction becomes viscous, 100 ml THF is added. After 5 hrs., solvent is removed to yield the product as a white powder. Magnesium monoethyl malonate crystallizes with one equivalent ethanol as solvate, and may be stored several weeks under inert atmosphere
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• Ireland , R. E. and Marshall , J. A. 1959 . J. Am. Chem. Soc. , 81 : 2907 See, for the acylation‐decarboxylation of magnesium monoethyl malonate yielding ß‐keto esters
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• Clark , R. D. and Heathcock , C. H. 1975 . J. Org. Chem. , 41 : 636 The chloroenone was prepared by the method of
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