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Non-defluorinative electrochemical silylation of ethyl trifluoroacetate: a practical synthesis of trifluoroacetyltrimethylsilane via its ethyltrimethylsilyl ketal |
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| Authors: | Michel Bordeau Philipe ClavelAlic Barba Muriel BerlandeClaude Biran Nicolas Roques |
| Affiliation: | a Laboratoire de Chimie Organique et Organométallique (UMR 5802 CNRS), Université Bordeaux 1, 351, cours de la Libération, F-33405 Talence cedex, France b Institute of Chemistry, Academy of Sciences, Academiei Str. 3, MD2028 Chisinau, Republic of Moldova c Rhodia Organique Fine, 85, avenue des frères Perret, BP 62, 69192 Saint-Fons, France |
| Abstract: | An efficient method for the preparation of original trifluoroacetyltrimethylsilane, CF3COSiMe3 (3), in two steps from readily available ethyl trifluoroacetate is described. Electrochemical reduction of this ester using a sacrificial anode and performed on a semimolar scale afforded the unprecedented corresponding ketal, CF3C(SiMe3)(OSiMe3)OEt (2) in 30-56% isolated yield. Treated with concentrated sulphuric acid at room temperature, the latter directly led to pure acylsilane 3 in 86% yield. |
| Keywords: | fluorine and compounds electrochemistry acylsilanes ketals silylation |
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