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Looking to remove the hydrazine byproduct left after the mitsunobu reaction. Using DIAD and polymer bound triphenyl phosphine. The reduced diad is coeluting with my product on silica. My thoughts for getting rid of it are trying an alumina column, acidic wash (I have an N-Boc so it can't be too acidic), or switching to a different azodicarboxylate.

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    $\begingroup$ can you provide drawing of your product? $\endgroup$ – permeakra Jul 22 '14 at 12:50
  • $\begingroup$ Unfortunately I cannot include a drawing. $\endgroup$ – Senderinator Jul 22 '14 at 14:06
  • $\begingroup$ Well, without any idea of what your product is, it is unlikely you will get an answer. $\endgroup$ – permeakra Jul 22 '14 at 15:04
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Acidic wash is not going to help. As you said you can try a DIAD alternative for example DCAD can give good results (sry no advertising intended here). There is also the option of taking your contaminated product to the next step(s) and hope you can get rid of the impurity there. I would take option A if I have to make a bunch of similar analogues by a Mitsunobu and B otherwise for not wasting too much time

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