DEPROTECTION OF SILYL ETHERS USING 2,3-DICHLORO-5,6-DICYANO-P-BENZOQUINONE

In the presence of a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), triethylsilyl (TES) and tert-butyldimethylsilyl (TBDMS) ethers are readily hydrolysed to the corresponding alcohols in MeCN-H2O (9:1) or tetrahydrofuran (THF)-H2O (9:1). TES ethers are cleaved to alcohols more ea...

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Bibliographic Details
Published inJournal of the Chemical Society, Perkin Transactions 1 no. 22; pp. 2997 - 2998
Main Authors TANEMURA, K, SUZUKI, T, HORAGUCHI, T
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 1992
Royal Society of Chemistry
Subjects
Chemistry
Chemistry, Organic
Exact sciences and technology
Organic chemistry
Physical Sciences
Science & Technology
Alcohol
Catalytic reaction
Ether
Silicon Organic compounds
Deprotection
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Summary:In the presence of a catalytic amount of 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ), triethylsilyl (TES) and tert-butyldimethylsilyl (TBDMS) ethers are readily hydrolysed to the corresponding alcohols in MeCN-H2O (9:1) or tetrahydrofuran (THF)-H2O (9:1). TES ethers are cleaved to alcohols more easily than TBDMS ethers. tert-Butyldiphenylsilyl (TBDPS) ethers are stable under these reaction conditions.
ISSN:0300-922X
2050-8255
1364-5463
DOI:10.1039/p19920002997