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20.5.15.1.1.14.1 Variation 1: Acylation of Methyl Acetoacetate with Acid Chlorides

DOI: 10.1055/sos-SD-020-01264

Beignet, J.Science of Synthesis, (2007201356.

The reaction of methyl acetoacetate with barium oxide (activated with water) generates a barium chelate complex 53 that adds smoothly to an acid chloride to afford a C-acylated complex 54. Treatment of the complex with methanol in situ produces an α-acylated β-oxo ester that undergoes deacetylation, and provides the corresponding methyl ­alkanoate 55, after an acidic workup (Scheme 24).[‌32‌] This method is efficient and amenable to large-scale syntheses. The use of calcium or strontium oxide is also possible, but more drastic reaction conditions have to be employed as these oxides are less basic than barium oxide.

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