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7.6.13.12 Method 12: Reactions Involving Diethyl (Ethoxymagnesio)malonate

DOI: 10.1055/sos-SD-007-00630

Shimizu, M.Science of Synthesis, (20047652.

Diethyl (ethoxymagnesio)malonate (4) (see Section 7.6.13.4) can be acylated by many activated carboxylic acid derivatives and alkyl chloroformates.[‌11‌] It is soluble in aprotic solvents such as diethyl ether and benzene, and undergoes exclusive C-acylation. A number of acylmalonates, e.g. 14, have been prepared from diethyl (ethoxymagnesio)malonate (Scheme 12).[‌39‌,‌40‌] Methyl ketones are prepared from the acyl malonate intermediate following vigorous hydrolysis (Scheme 12).[‌41‌] Methanetricarboxylic esters are generally prepared by the reaction of diethyl (ethoxymagnesio)malonate with an alkyl chloroformate.[‌11‌] For example, triethyl methanetricarboxylate is obtained in high yield from diethyl (ethoxymagnesio)malonate and ethyl chloroformate.

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