Synthesis of 3-acetonyl- and 3-(2-oxoethyl)glutarates

Several synthetic routes to 3-acetonyl- and 3-(2-oxoethyl)glutarates have been explored. The most advantageous involves, as the key steps, the conjugate addition of an appropriately substituted vinylmagnesium bromide to an alkylidenemalonic ester, a bis-homologation of the resulting diester and, finally, the reductive ozonolysis of the carbon–carbon double bond. The synthesis can be satisfactorily conducted in good overall yield on a multigram scale.