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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: sharbeldam on May 05, 2023, 04:40:58 PM

Title: Any ways to transoform beta keto ester to enone?
Post by: sharbeldam 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? :/

Title: Re: Any ways to transoform beta keto ester to enone?
Post by: rolnor 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.

Title: Re: Any ways to transoform beta keto ester to enone?
Post by: Vidya 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.

Title: Re: Any ways to transoform beta keto ester to enone?
Post by: sharbeldam 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

Title: Re: Any ways to transoform beta keto ester to enone?
Post by: Vidya on May 15, 2023, 01:37:01 AM

Ester group can be added again.