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Re: ORGLIST: NaH reaction

From: Andrew Molder <andrew.molder>
Subject: Re: ORGLIST: NaH reaction
Date: Wed, 27 Jun 2012 13:46:08 -0500

I know that the polymer industry is a black sheep to through natural products crowd but we acutually adjust the viscosity of  some of our curing agents based on the deprotonation of various phenols by the various amines contained.  could be some complexation of your pyridine moiety with your phenol.  May want to first form your phenoxide then titrated in your pyridine to minimize side reactions.  Keep your kinetic vs. thermodynamic products in mind.  Let me know how it goes.

Andy

On Jun 27, 2012 1:12 PM, "vinutha hanumaiah" <vinutha.bl> wrote:
Hi all,
 
Am doing a regioselective reaction with  2- chlorophenol and a substituted pyridine in DMF.  It seems the phenol is not deprotonated completely in the reaction ending up with less yield. Is it possible to heat the reaction mixture? I have never done heating with NaH. Please can anyone suggest me anyother strong base for deprotonation of phenol or suggest ideas to improve yeilds?
 
Thanks, 
Thanu 
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