For a click reaction, silica or alumina column are not suitable for my solution.
If the product is ether soluble it could be extracted into ether and the copper can then be removed by washing with 25% ammonium chloride,
Are you sure that all silicas are not OK, a thiol SAMMS is a silica but it should have very few Si-OH groups left as it has a monolayer of mercapto propyl groups on it, it will bind very strongly to copper.
Very effective catalyst for this type of reaction is recyclable Cu (I) supported on a weakly acidic cation-exchanger polyacrylate resin (Tau-Chem Ltd.. Bratislava, Slovakia). Very simple separation of catalyst from reaction mixture after reaction by filtration.
Your problem is DMF. Assuming that your product is soluble in ether:
Charge 3-4 volume of brine (wrt the amount of DMF) and 3-4 volume of ether (or MTBE). Mixed well. Allow the mixture to settle. Precipitation of a crystalline white solid (NaCl) would occur. Remove the lower layer and the solid. Repeat the washing of the upper organic layer with same volume of brine (2-3 times). The residual amount of DMF remain in the ether layer should be < 5% at this point. Now wash the organic layer with ammonium hydroxide until the aqueous layer is no longer blue.
Remove DMF by evaporation under high vacuum, following step depend on your compounds or materials. In polymer case you can use precipitation in solvent.
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