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26.1.4.4.10 Variation 10: With Organolithium or Organosodium Reagents

DOI: 10.1055/sos-SD-026-00142

Figadère, B.; Franck, X.Science of Synthesis, (200526271.

Acylation of organolithium reagents with carboxylic anhydrides is not frequently used because of the reactivity with the organometallic of the ketone formed, which gives rise to alcohols. To minimize this side reaction,[‌194‌] 2 equivalents of the anhydride (e.g., phthalic anhydride) are used and yields increase to 87%, whereas the use of only 1 equivalent of the anhydride gives the expected ketone in only 35% yield.

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References