How do I get rid of TBAF?
Having demonstrated that a combination of sulfonic acid resin and calcium carbonate can effectively remove TBAF from THF solution, we then studied the effectiveness of this workup method of TBAF-promoted TBS deprotection.
What is TBAF in organic chemistry?
Tetra-n-butylammonium fluoride (TBAF): A quaternary alkylammonium salt, commonly used to deprotect silyl ethers. Molecular structure of tetra-n-butylammonium fluoride.
Is TBAF a base?
In contrast to these bases, tetrabutylammonium fluoride (TBAF) is moderately basic, highly soluble in organic solvents, and weakly nucleophilic. Based on these results, TBAF should be considered as the preferred base for (11) C-methylation reactions using 1.
Why is TBAF basic?
Because the fluoride ion is such a strong hydrogen bond acceptor, its salts tend to be hydrated and of limited solubility in organic solvents. As a fluoride source in organic solvents, TBAF is used to remove silyl ether protecting groups. It is also used as a phase transfer catalyst and as a mild base.
How do you remove Tbaf from a reaction mixture?
Dissolve your mixture in diethylether. TBAF is also soluble in Et2O. Now you can use the fact that TBA-chloride is not soluble in Et2O and wash your mixture several times with NH4Cl. This will remove tetrabutylammonium salts completely for sure.
How do I get rid of tetrabutylammonium bromide?
Dissolve the solid in Ethyl acetate and wash the organic layer with water to separate TBAB. After water wash dried the organic layer with anhydrous sodium sulfate and evaporate the organic layer under reduced pressure to get pure compound.
What is TBAF reagent?
Tetrabutylammonium fluoride (TBAF) can be used as a reagent: For the deprotection of silyl and N-sulfonyl groups. In the fluorination reactions. To synthesize 2-substituted indoles by cyclization reaction of various 2-ethynylanilines with terminal alkynes using Pd catalyst.
What does TBAF stand for?
TBAF
| Acronym | Definition |
|---|---|
| TBAF | The Bubel/Aiken Foundation |
| TBAF | Tetra-n-butylammonium fluoride |
| TBAF | Tampa Bay Advertising Federation (Tampa Bay, FL) |
| TBAF | T-Bill Accrual Factor (investment appreciation) |
What is Tbaf reagent?
Is Tbaf water soluble?
Alternate Name: TBAF. Physical Data: TBAF·xH2O: mp 62–63 °C. Solubility: sol H2O, THF, MeCN. Form Supplied in: trihydrate, 1.0 M solution in THF, and 75 wt % solution in water.
What does Tbaf stand for?
What is TBAB used for?
Tetrabutylammonium bromide (TBAB) is a quaternary ammonium salt with a bromide commonly used as a phase transfer catalyst. It is used to prepare many other tetrabutylammonium salts by salt metathesis reactions.
Does anyone know how to dissolve TBAF with FCC?
FCC did not work at all. Solution (at least it worked for me): after FCC, I dissolved my product with TBAF in water and pass it through a Supelco SPE DSC-C8 3 mL, 500 mg for up to 10 mg of my compound. Use only water and do it slowly. I always get the desired compound from tube one to 6-7 and no TBAF is present.
How do you prepare TBAF from silyl ether?
A stock solution of TBAF in acetic acid is prepared (0.15 mL of HOAc per 1.0 mL of 1M TBAF in THF). The silyl ether is dissolved in THF and reacted with an excess of the stock solution for several hours.
Why is TBAF used as a Floride anion source?
Also, TBAF is mostly used as the floride anion source because its solubility in organic solvent. Other fluoride anion source like KF can be used as alternative to TBAF with proper solvent. Thanks for contributing an answer to Chemistry Stack Exchange! Please be sure to answer the question.
How to prepare silver halide from TBAF?
The exchange of counter ion can be accomplished by dissolving TBAF in acetonitrile, followed by addition of an equimolar amount of silver tetrafluoroborate. After stirring at room temperature for 15 minutes, the precipitate of silver halide is filtered off over high flow. Then the filtrate is concentrated in vacuo.