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Topic: Mesylation of pyridinedimethanol  (Read 2365 times)

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Offline p_rus

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Mesylation of pyridinedimethanol
« on: January 29, 2013, 04:51:28 PM »
Hello, this is my first post.

I am trying to mesylate bis(-CH2OH)pyridine with MsCl and Et3N in CH2Cl2.
The analogous reaction with bis(CH3CH(OH)-)pyridine goes very well, but in this case I encounter two problems:
1. The compound is very scarcely soluble in the solvent
2. The formed mesylate easily undergoes substitution by the chloride, so that I'm left at the end with a lot of either unreacted alcohol or alkyl chloride depending on the reaction time.
Does anyone know a workaround to this problem? I've thought of using an inorganic base (potassium carbonate?) to sequester the chloride but I'm not very sure about it.

Offline discodermolide

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Re: Mesylation of pyridinedimethanol
« Reply #1 on: January 29, 2013, 05:02:41 PM »
I think you need a different base here, as you say pot. carb. may be ok.
Try an ether solvent, diisopropyl ether at reflux.
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