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Topic: Any ways to transoform beta keto ester to enone?  (Read 1019 times)

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Offline sharbeldam

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Any ways to transoform beta keto ester to enone?
« on: May 05, 2023, 04:40:58 PM »
I have been thinking about this for 4 hours.
My only attempt is adding a strong base to deprotonate, but then i can only add R group or do decarboxylation.
I cant add a halogen and eliminate it i would guess....
so what i do? :/
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Offline rolnor

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Re: Any ways to transoform beta keto ester to enone?
« Reply #1 on: May 06, 2023, 10:55:06 AM »
You can use benzeneselenylchloride/Base first then oxidize to the selene oxide with H2O2 and this eliminates spontaneously . not sure what base is good, TEA? Its a very acidic position https://en.wikipedia.org/wiki/Selenoxide_elimination#:~:text=Elimination%20of%20selenoxides%20takes%20place%20through%20an%20intramolecular,-selective%20when%20acyclic%20%CE%B1-phenylseleno%20carbonyl%20compounds%20are%20employed.

Offline Vidya

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Re: Any ways to transoform beta keto ester to enone?
« Reply #2 on: May 13, 2023, 01:18:34 AM »
You can do alpha halogenation I think.
Remove acidic alpha H(to ketone and ester) using a base and add H2O with Br2 .
Remove Br by dehydrohalogenation process.

Offline sharbeldam

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Re: Any ways to transoform beta keto ester to enone?
« Reply #3 on: May 13, 2023, 07:38:15 PM »
The water would hydrolize the ester i think
and thanks rolnor, i read that way, i was thinking something o-chem 1/2 related and they dont teach that way
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Offline Vidya

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Re: Any ways to transoform beta keto ester to enone?
« Reply #4 on: May 15, 2023, 01:37:01 AM »
Ester group can be added again.

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