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Topic: Deprotection of a carboxylate ester in presence of a boronic ester?  (Read 2487 times)

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Offline teiwaz

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Deprotection of a carboxylate ester in presence of a boronic ester?
« 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
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Offline phth

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Re: Deprotection of a carboxylate ester in presence of a boronic ester?
« Reply #1 on: December 22, 2016, 12:05:59 AM »
Is it possible to use SciFinder?
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Offline rolnor

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Re: Deprotection of a carboxylate ester in presence of a boronic ester?
« Reply #2 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.
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Offline Dan

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Re: Deprotection of a carboxylate ester in presence of a boronic ester?
« Reply #3 on: December 22, 2016, 09:18:35 AM »
Possibly helpful (I haven't read it): http://pubs.acs.org/doi/abs/10.1021/jo400617j
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