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Re: ORGLIST: NaH reaction

From: Andrew Molder <andrew.molder>
Subject: Re: ORGLIST: NaH reaction
Date: Wed, 27 Jun 2012 13:34:01 -0500

Hydride ion is very stubborn about solubility. You may want to consider trying hydrides with different counter ions .Complexation of your counter ion can change your stereochem. 

Also what about hunig's base BuLi LDA, KOH, etc...? 

Btw did you solve your dmf issues?  I came across the dmf azeotrope I was trying  remember.  Dmf and xylene azeotrope and there is a ton of lit. on it.

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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