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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: p_rus on January 29, 2013, 04:51:28 PM

Title: Mesylation of pyridinedimethanol
Post by: p_rus 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.

Title: Re: Mesylation of pyridinedimethanol
Post by: discodermolide 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.