Silyl ether removed
Fluoride cleaves the silicon–oxygen bond, leaving the alcohol.
What it needs, and what it gives
- Reaction class
- Deprotection
- Tetrabutylammonium fluoride. Neither acid nor hydrogen will do it.
- not stated
- Mechanism
- Fluoride removal of a silyl group, 2 steps
How it is thought to happen
Fluoride attacks the silicon, which is where it would rather be than anywhere else, and the alcohol is released.
- Fluoride attacks the silicon
- The alkoxide takes a proton
Try it on your own structures
Enter your reactants in the Reaction Lab. If this transformation matches what you drew, it is applied and the outcome is shown next to the records that back it — with the count of documented reactions doing the same thing on substrates like yours, rather than a confidence score.
Other deprotection transformations
Boc removed from an amine
Acid takes the carbamate off, leaving the free amine.
Cbz removed from an amine
Hydrogen over a metal cleaves the benzyl carbamate, leaving the free amine.
Benzyl ether removed
Hydrogen over a metal cleaves the benzyl ether, leaving the alcohol.
Fmoc removed from an amine
A secondary amine takes the acidic hydrogen and the group falls away.
Demethylation of an aryl methyl ether
The methyl is taken off an aromatic methyl ether, leaving the phenol.