I am running a Stille coupling using an excess of 2-tributylstannyl pyridine and having a hard time purifying my product because of the tin byproduct and the excess reagent. I have tried washing with KF aq. solution and treating with NaOH to form Bu3SnOH and it did not help. Any alternative ways that could help ?
http://chem.chem.rochester.edu/~nvd/pages/workup.php?page=removing_tin
it looks like you have tried 2 of the 6 suggested here. Maybe the other options will work.
http://pubs.acs.org/doi/abs/10.1021/acs.chemrev.5b00196?journalCode=chreay
This review may help too.
Good luck!
Byproducts of tin based reactions such as Bu3SnBr can be removed by treatment with AlMe3 to create the nonpolar Bu3SnMe or NaOH to create the polar Bu3SnOH. See: P. Renaud, E. Lacote, L. Quaranta Tetrahedron Lett. 1998 , 39 , 2123.
Use a tin free reagent. You will never achieve a complete removal (at least for pharmaceutical/biological purposes).
Thanks Eugene Yang for the review article. It was very helpful. Partitioning between hexane and acetonitrile worked really well for me
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