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Chemistry Forums for Students => Organic Chemistry Forum => Organic Chemistry Forum for Graduate Students and Professionals => Topic started by: teiwaz on December 21, 2016, 06:39:07 PM

Title: Deprotection of a carboxylate ester in presence of a boronic ester?
Post by: teiwaz on December 21, 2016, 06:39:07 PM

hi all,

a short question: is it possible to deprotect a carboxylic ester (ethyl ester) in presence of a boronic ester (pinacol ester)? I would like to keep the boronic ester due to cloumn chromatography as a possible purification method but i have kind of no experiences with boronic esters and how fast they get hydrolyzed with NaOH/LiOH.

thx

Title: Re: Deprotection of a carboxylate ester in presence of a boronic ester?
Post by: phth on December 22, 2016, 12:05:59 AM

Is it possible to use SciFinder?

Title: Re: Deprotection of a carboxylate ester in presence of a boronic ester?
Post by: rolnor on December 22, 2016, 09:04:20 AM

I think boronic esters are more sensitive to base than carboxylic esters but i have no hands on experience.

Title: Re: Deprotection of a carboxylate ester in presence of a boronic ester?
Post by: Dan on December 22, 2016, 09:18:35 AM

Possibly helpful (I haven't read it): http://pubs.acs.org/doi/abs/10.1021/jo400617j