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Topic: Reducing esters without reducing ketones in the same compound. How?  (Read 3585 times)

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Offline miss_science

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The compound has a ketone on one end and an ester on the other end.

I proposed to turn the ketone into an acetal to protect it but
a) will the c=o of the aldehyde also turn into an acetal
b) I need to turn aldehyde into an alcohol using a hydride, which will violently react with water produced with the acetal.

What do you propose as a new protecting group for the ketone alone, or if there's a better reaction to keep the ketone while turning the aldehyde to
an alcohol?

Offline Honclbrif

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Re: Reducing esters without reducing ketones in the same compound. How?
« Reply #1 on: August 02, 2011, 03:07:52 PM »
a) You switched half way from ester to aldehyde, which one do you mean? It makes a pretty big difference.
b) Use a desiccant to remove the water first, or Dean-Stark conditions to remove water while you form the acetal
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Offline discodermolide

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Re: Reducing esters without reducing ketones in the same compound. How?
« Reply #2 on: August 02, 2011, 03:38:03 PM »
The compound has a ketone on one end and an ester on the other end.

I proposed to turn the ketone into an acetal to protect it but
a) will the c=o of the aldehyde also turn into an acetal
b) I need to turn aldehyde into an alcohol using a hydride, which will violently react with water produced with the acetal.

What do you propose as a new protecting group for the ketone alone, or if there's a better reaction to keep the ketone while turning the aldehyde to
an alcohol?
Please be much more specific about the compounds in involved here, I am confused by your question.
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Offline miss_science

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Re: Reducing esters without reducing ketones in the same compound. How?
« Reply #3 on: August 02, 2011, 03:44:21 PM »
a) You switched half way from ester to aldehyde, which one do you mean? It makes a pretty big difference.
b) Use a desiccant to remove the water first, or Dean-Stark conditions to remove water while you form the acetal

sorry, I meant ester not aldehyde.

I want to react the acyl group of the ester with a hydride
nucleophile which can't have water.

Strictly speaking, I just want to write a synthesis on paper, not perform in a lab so how can I include a desicant as a compound/reagent/solvent?

Offline Honclbrif

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Re: Reducing esters without reducing ketones in the same compound. How?
« Reply #4 on: August 02, 2011, 04:11:56 PM »
Strictly speaking, I just want to write a synthesis on paper, not perform in a lab so how can I include a desicant as a compound/reagent/solvent?

You're getting to caught up in particulars. Since its all on paper, you can just draw an arrow and write something like "desiccant" or "-H2O", or "Dean-Stark" under it. Otherwise, you seem to be on the right path.
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