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Please login to access the full content or check if you have access via Variation 1: Using a Reformatsky Reagent and an Acid Chloride

DOI: 10.1055/sos-SD-020-01264

Beignet, J.Science of Synthesis, (2007201351.

The reaction between the Reformatsky reagent derived from ethyl bromoacetate and an acid chloride may produce the corresponding β-oxo ester; however, the yield depends upon the reaction conditions and the choice of the substrate. Thus, the synthesis of an α-unsubstituted 3-oxoalkanoate is limited by the acidity of the product; this leads to the consumption of the Reformatsky reagent acting as a base.[‌23‌] Fortunately, the use of a palladium(0) catalyst improves matters, and allows the formation of the desired β-oxo ester 36 (Scheme 15). This procedure is useful with aromatic acid chlorides, but rather low yielding with aliphatic acid chlorides. In such cases, slightly improved results are obtained by treating the acyl chloride with ethyl bromoacetate in the presence of both zinc and the palladium catalyst.[‌23‌] No experimental details are available.

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