Sciencemadness Discussion Board

Aqueous TBAF Deprotection of Alcohols

hstraley - 25-7-2016 at 21:41

Anybody have any recommendations for using TBAF as a solution in water as a means of deprotecting silyl groups to form the alcohol? It's cheaper, and would be nice to use instead of the 1M solution in THF.
Thanks!

Metacelsus - 26-7-2016 at 05:04

If your compound is water-soluble, you might as well use ammonium fluoride (or another inorganic fluoride). I've run deprotections of TMS-alkynes with saturated KF in methanol, and those conditions might also work for alcohols.

Dr.Bob - 26-7-2016 at 18:45

Just remember that TBAF in water is quite basic, and may react with other groups. If it is TMS, it will come off with anything, if TBDMS then it take more work.