Selective Protection of Secondary Alcohols by Using Formic Acid as a Mild and Efficient Deprotection Reagent for Primary tert-Butyldimethylsilyl Ethers
Document Type
Article
Publication Date
3-19-2019
Department
Chemistry and Biochemistry
School
Mathematics and Natural Sciences
Abstract
A mild, efficient, and environmentally friendly method for the selective protection of secondary hydroxyl groups is described. The method involves the protection of both primary and secondary hydroxyl groups as tert-butyldimethylsilyl (TBDMS) ethers and selective deprotection of the primary TBDMS group with formic acid in acetonitrile/water. The rates of desilylation of primary and secondary TBDMS ethers by different concentrations of formic acid are determined. Formic acid of 5–20% concentration is found to selectively deprotect primary TBDMS ethers while keeping more than 95% of their secondary counterparts intact.
Publication Title
Synlett
Volume
30
Issue
16
First Page
1895
Last Page
1898
Recommended Citation
Sapotka, K.,
Huang, F.
(2019). Selective Protection of Secondary Alcohols by Using Formic Acid as a Mild and Efficient Deprotection Reagent for Primary tert-Butyldimethylsilyl Ethers. Synlett, 30(16), 1895-1898.
Available at: https://aquila.usm.edu/fac_pubs/16887