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

VH Jadhav, SB Lee, HJ Jeong, ST Lim, MH Sohn…

Index: Jadhav, Vinod H.; Jeong, Hwan-Jeong; Lim, Seok Tae; Sohn, Myung-Hee; Kim, Dong Wook Organic Letters, 2011 , vol. 13, # 9 p. 2502 - 2505

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Citation Number: 8

Abstract

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 ...