104155-55-7Relevant academic research and scientific papers
Enol Ethers, XVII. Acylation of Trimethylsilyl Enol Ethers with Malonyl Dichloride - Synthesis of 4-Hydroxy-2H-pyran-2-ones
Effenberger, Franz,Ziegler, Thomas,Schoenwaelder, Karl-Heinz,Kesmarszky, Thomas,Bauer, Bernd
, p. 3394 - 3404 (2007/10/02)
Trimethylsilyl enol ethers of aldehydes 1, acyclic and cyclic ketones 4 and 10, respectively, are acylated by malonyl dichloride (2) at room temperature or even at -60 deg C.After aqueous workup, the 6-unsubstituted 4-hydroxy-2H-pyran-2-ones 3 are obtained from 1-(trimethylsiloxy)alkenes 1, whereas the 5,6-alkylene-bridged 4-hydroxy-2H-pyran-2-ones 11 are formed from 1-(trimethylsiloxy)cycloalkenes 10.Acylation of 2-(trimethylsiloxy)-1-propene (4a) and 3-(trimethylsiloxy)-2-pentene (4b) results in mixtures of 4-(trimethylsiloxy)-2H-pyran-2-ones 5 (main products) and phloroglucinol tris(trimethylsilyl) ethers (6) (by-products).
