Mild Deprotection of TBDMS Ethers
RO-TBDMS → ROH
TBDMS ethers are very useful protecting groups in organic synthesis and there are already many methods for their removal, but this latest deprotection method is particularly mild. The TBDMS ether is simply stirred in methanol with Fe(OTs)3 (2 mol %) at room temperature for typically 2-4 hours, although some more hindered ethers require extended reaction times (up to 24 hours).
The reaction is worked up by partitioning between ethyl acetate and aqueous sodium bicarbonate solution. Yields are 70-90% with most yields being in the range 77-84%.
J.M. Bothwell, V.V. Angeles, J.P. Carolan, M.E. Olson, and R.S. Mohan*, Tet. Letts., 2010, 51, 1056-1058.