Yesterday I did a Cu-catalyzed azide-alkyne cycloaddition with CuI, in DMF, at 80*C, over night. I put ether into my homogeneous mixture to force my
product to precipiate, and I isolated it by filtration.
The problem is there is Cu residual in my precipitate, so my precipitate is a bit green.
Then, I put it through a silica column to take out the Cu, but my precipitate is still green.
My reagents are soluble in ether, and my product is not (!), so i want to keep
this solvant.
Anyone have a solution to take out the Cu / improve my reaction? Thank you!
[Edited on 21-6-2013 by Carabistouilles]
[Edited on 21-6-2013 by Carabistouilles]ElectroWin - 20-6-2013 at 18:33
distill the spent solvent?Carabistouilles - 20-6-2013 at 18:56
I didpolymerguy - 20-6-2013 at 20:18
It'd be helpful to know some sort of structure of the product that you are expecting, or a reaction scheme.
Also, you say that your product is soluble in ether, but that it precipitated upon addition of ether to the reaction mixture? That doesn't make sense
to me.sonogashira - 21-6-2013 at 02:41
It'd be helpful to know some sort of structure of the product that you are expecting, or a reaction scheme.
Also, you say that your product is soluble in ether, but that it precipitated upon addition of ether to the reaction mixture? That doesn't make sense
to me.
it's a dendrimeric structureDr.Bob - 21-6-2013 at 06:10
If your compound is not water soluble, then wash the solid product with water, Aq. EDTA, Ammonia or some other copper chelator. Otherwise,
recrystallize the product from another aprotic organic solvent and filter while hot. If your product can chelate copper, then you may have a
problem. Triazoles are normally not that soluble, depending on the substituents. Carabistouilles - 21-6-2013 at 16:11
If your compound is not water soluble, then wash the solid product with water, Aq. EDTA, Ammonia or some other copper chelator. Otherwise,
recrystallize the product from another aprotic organic solvent and filter while hot. If your product can chelate copper, then you may have a
problem. Triazoles are normally not that soluble, depending on the substituents.
Yesterday I did a Cu-catalyzed azide-alkyne cycloaddition with CuI, in DMF, at 80*C, over night.
Just curious, what type of 1,2,3-triazole derivative did you make?ElectroWin - 22-6-2013 at 05:01
are you sure it's traces of copper remaining?
maybe take a portion and see if a little phosphoric acid will precipitate the copper?AndersHoveland - 22-6-2013 at 15:49
Another possibility you might want to consider is that the triazole has formed an insoluble salt with the copper. That would explain why you are
having difficulty separating it out.
!), so i want to keep
this solvant. 