hstraley
Harmless
Posts: 1
Registered: 25-7-2016
Member Is Offline
Mood: No Mood
|
|
Aqueous TBAF Deprotection of Alcohols
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
International Hazard
Posts: 2539
Registered: 26-12-2012
Location: Boston, MA
Member Is Offline
Mood: Double, double, toil and trouble
|
|
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
International Hazard
Posts: 2734
Registered: 26-1-2011
Location: USA - NC
Member Is Offline
Mood: No Mood
|
|
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.
|
|
|
![[*]](images/xpblue/default_icon.gif){kind=icon}
