Non-defluorinative electrochemical silylation of ethyl trifluoroacetate: a practical synthesis of trifluoroacetyltrimethylsilane via its ethyltrimethylsilyl ketal

Autor:	Muriel Berlande, Nicolas Roques, Alic Barba, Philippe Clavel, Claude Biran, Michel Bordeau
Rok vydání:	2003
Předmět:	chemistry.chemical_compound chemistry Silylation Galvanic anode Yield (chemistry) Organic Chemistry Drug Discovery Organic chemistry Electrochemistry Biochemistry Acylsilane
Zdroj:	Tetrahedron Letters. 44:3741-3744
ISSN:	0040-4039
Popis:	An efficient method for the preparation of original trifluoroacetyltrimethylsilane, CF 3 COSiMe 3 ( 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, CF 3 C(SiMe 3 )(OSiMe 3 )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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::b5cb27bf58e8dced7ec9679b812d11da https://doi.org/10.1016/s0040-4039(03)00745-7 Zobrazit plný text záznamu Full Text from ScienceDirect