High-yielding method for preparation of carbocyclic or N-containing heterocyclic β-keto esters using in situ activated sodium hydride in dimethyl sulphoxide

Green Chemistry Letters and Reviews

Jelena Popović-Djordjević¹ 

关键词: Acylation;    condensation reaction;    environmentally benign solvent;   

DOI  :  10.1080/17518253.2016.1145744

学科分类：化学（综合）

来源: Taylor & Francis

【 摘 要 】

It was found that NaH suspension in DMSO was highly activated when reacted with an alcohol. The in situ generated NaH/alkoxide mixture permitted very rapid and complete deprotonation and acylation of various cyclic ketones with alkyl carbonates at ambient temperature. Activated NaH/alkoxide in DMSO is particularly effective in Dieckmann condensations, where it affords 5- and 6-membered carbocyclic or N-containing heterocyclic β-keto esters in high yields. A heterocyclic Dieckmann condensation was performed on a molar scale, demonstrating the scalability of the procedure. Besides, DMSO is non-toxic, relatively inexpensive and environmentally benign solvent.

【 授权许可】

Unknown