An Efficient and Chemoselective Deprotection of Aryl <i>tert</i>-Butyldimethylsilyl (TBDMS) Ethers by NaCN

Qiao, Xue-jun; Hou, Xiao; Fang, Wu-hong; Bao, Xue-fei; Chen, Guo-liang

doi:10.5935/0103-5053.20150342

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Articles • J. Braz. Chem. Soc. 27 (5) • May 2016 • https://doi.org/10.5935/0103-5053.20150342 linkcopy

An Efficient and Chemoselective Deprotection of Aryl tert-Butyldimethylsilyl (TBDMS) Ethers by NaCN

Authorship SCIMAGO INSTITUTIONS RANKINGS

Abstract

Phenolic tert-butyldimethylsilyl (TBDMS) ethers can be deprotected to yield phenols in excellent yield using sodium cyanide (NaCN) as catalyst in ethanol. The deprotectation of various phenolic TBDMS ethers were found to be very convenient, fast, high yielding and chemoselective.

Keywords:
deprotectection; tert-butyldimethylsilyl; sodium cyanide

entry	Solvent	time / h	Yield / %
1	EtOH + 1 mL H₂O	1.0	86.4
2	THF	−	−
3	DMF	−	−
4	acetone	−	−
5	toluene	−	−
6	EtOH	8.0	56.7
7	EtOH + 0.5 mL H₂O	4.0	73.5
8	EtOH + 2 mL H₂O	0.8	86.9
9	EtOH + 5 mL H₂O	0.8	87.1

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[TFN01] EtOH: ethanol; THF: tetrahydrofuran; DMF: N,N-dimethylformamide.