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Topic: reduction of ester to alcohol?  (Read 4595 times)

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Offline shrikantvarma

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reduction of ester to alcohol?
« on: March 05, 2011, 07:48:29 AM »
my compound have lactone & ester ,i want to reduce ester to alcohol what will be ideal reagent for this conversion?

thanks

Offline Dan

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Re: reduction of ester to alcohol?
« Reply #1 on: March 05, 2011, 08:10:26 PM »
The reactivities will be similar so you're going to have problems, it would be good to have more information because it isn't really possible to estimate their relative reactivity without more structural detail. What kind of ester and lactone do you have, how hindered are they? 
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Offline Honclbrif

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Re: reduction of ester to alcohol?
« Reply #2 on: March 08, 2011, 06:02:09 PM »
If the lactone is hindered, or a relatively stable 5- or 6-membered lactone, and the ester is relatively unhindered, there may be some options.

You could try mild hydrolysis conditions to hydrolyze the ester (if unhindered) to yield a carboxylate. From there you may be able to try a diborane reduction. I recall reading somewhere that it will reduce a carboxylate to an alcohol but leave esters alone. No guarantees tho, look it up yourself before attempting. If hydrolysis does not work you may also be able to transesterify the ester with t-butanol, then deprotect with acid and try the diborane.

Alternatively, you could try to transthioesterify the ester with a thiol, then try a Fukuyama reduction to yield an aldehyde. From there, selectively reducing the aldehyde with NaBH4 should be fairly straightforward

Lactones and esters have very similar reactivities so you may have painted yourself into a corner. Without seeing some structures, its hard to tell which way to go.
Individual results may vary

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