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Synlett 1991; 1991(6): 407-409
DOI: 10.1055/s-1991-20744
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A Convenient Route to 2,2-Disubstituted 4-Pentynoic Acids from Meldrum's Acid

Antonio Arcadi* , Sandro Cacchi, Monica Delmastro, Fabio Marinellia
  • *Dipartimento di Chimica, Ingegneria Chimica e Materiali, Università degli Studi, V. Assergi 4, I-67100 L'Aquila, Italy
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Publication Date:
07 March 2002 (online)

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A three-step procedure for the preparation of 2-substituted 2-methoxycarbonyl-4-pentynoic acids starting from Meldrum's acid (2,2-dimethyl-1,3-dioxane-4,6-dione) was developed (10 examples). The method is based on the mono-alkylation of Meldrum's acid, propargylation of the monoalkyl derivative in the presence of potassium carbonate at room temperature, and treatment of the disubstituted Meldrum's acid with sodium methoxide at room temperature.