[p_rus]

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.

[discodermolide]

I think you need a different base here, as you say pot. carb. may be ok.
Try an ether solvent, diisopropyl ether at reflux.