An efficient and chemoselective deprotection of tert-butyldimethylsilyl (TBDMS) ethers using tailor-made ionic liquid

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• 作者：Vinod H. Jadhav ; Sang Bong Lee ; Hwan-Jeong Jeong ; Seok Tae Lim ; Myung-Hee Sohn ; Dong Wook Kim ; ^{kimdw@chonbuk.ac.kr}
• 关键词：Chemoselective deprotection ; Desilylation ; tert-Butyldimethylsilyl group ; Ionic liquid ; tert-Alcohol ; Fluoride
• 刊名：Tetrahedron Letters
• 出版年：2012
• 期刊代码：109_00404039
• 类别：ch
• 出版时间：18 April, 2012
• 卷：53
• 期：16
• 页码：2051-2053
• 文件大小：462 K

摘要

Phenolic tert-butyldimethylsilyl (TBDMS) ethers can be deprotected to yield phenols in excellent yield using tailor-made ionic liquid [dihexaEGim][OMs] (dihexaEGim = dihexaethylene glycolic imidazolium salt) as an organic catalyst with alkali-metal fluoride in tert-amyl alcohol. On the contrary, all TBDMS protecting groups can be cleaved cleanly from the bis-TBDMS ether using the same reaction in CH₃CN solvent instead of tert-alcohol at 100 掳C. This [dihexaEGim][OMs]/tert-amyl alcohol media system allows the highly selective phenolic deprotection reaction of various bis-TBDMS ethers containing both phenolic and aliphatic TBDMS ethers to provide the corresponding phenols in high yield.