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Synlett 1990; 1990(7): 408-410
DOI: 10.1055/s-1990-21108
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The Electrochemical Reduction of Ethyl 4-Hydroxy-2-alkynoates: An Example of Selective trans Reduction of Carbon-Carbon Triple Bonds in a Slightly Acidic Medium

Antonio Arcadi, Sandro Cacchi, Italo Carelli, Antonella Curulli, Achille Inesi, Fabio Marinelli
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Publikationsdatum:
08. März 2002 (online)

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The electrochemical reduction of ethyl 4-hydroxy-2-alkynoates 1 (5 examples) in the presence of a twofold excess of benzoic acid as the proton donor produces selectively ethyl (E)-4-hydroxy-2-alkenoates in good yield. The outcome of the reaction depends upon the amount of benzoic acid used. Omitting it, decomposition of 1 to the parent ketones and ethyl propynoate is observed while in the presence of a fourfold excess the reaction gives the corresponding saturated esters 7.