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Aart Van Beuzekom

Dess–Martin oxidation work up

I'm doing an oxidation of an alcohol with Dess–Martin periodinane which works really well but having trouble with the work up. Doing this reaction with about 5 g of alcohol so the reaction ends up using about 17 g of DMP. As the reaction progresses the DMP byproduct crashes out. And working up turns it into a gun that is quite difficult to remove

Running reaction in DCM and work up with bicarb. Even after filtration DMP is still present. Separates fine on a column but with how much there is it seems to be trappings some of my product. I've read that a thiosulphate wash is also used in these reactions, but I don't think this will be useful to get rid of the gum.

Any suggestions?

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