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Synlett 1995; 1995(1): 45-46
DOI: 10.1055/s-1995-4879
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Direct Conversion of p-Methoxybenzyl Ethers into Silyl-protected Alcohols by the Action of Trialkylsilyl Trifluoromethanesulfonate and Triethylamine

Takeshi Oriyama* , Kaori Yatabe, Yuzo Kawada, Gen Koga
  • *Department of Chemistry, Faculty of Science, Ibaraki University, Bunkyo, Mito 310, Japan
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Publication History

Publication Date:
31 December 2000 (online)

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The combined use of t-butyldimethylsilyl trifluoromethanesulfonate and triethylamine cleaves readily p- or o-methoxybenzyl ethers to give directly the corresponding t-butyldimethylsilyl ethers in high yields thus affording an expedient way to replace the benzyl ether-type protective group with the silyl ether-type one.

p-methoxybenzyl ether - silyl ether - chemoselective - trialkylsilyl trifluoromethanesulfonate