June 07, 2020, 03:25:31 AM
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Topic: Enolate chemistry  (Read 301 times)

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Offline confusedug45

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Enolate chemistry
« on: May 18, 2020, 10:50:57 AM »
So I believe the 1-(lithiooxy)-1-methoxyethene is acting either as a base or as a soft nucleophile. I've tried attacking various carbonyls on the chain but cannot attain the desired product. Any help would be greatly appreciated, thank you.

Offline kriggy

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Re: Enolate chemistry
« Reply #1 on: May 19, 2020, 12:48:58 AM »
What about aldol reaction?

Offline confusedug45

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Re: Enolate chemistry
« Reply #2 on: May 19, 2020, 05:26:27 AM »
It looks like an aldol reaction and the aldehyde part would be the most electrophilic but it doesn't get the right product unless there is an additional step. I think it might be an aldol then rearrangement

Offline kriggy

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Re: Enolate chemistry
« Reply #3 on: May 20, 2020, 02:21:57 AM »
It looks like an aldol reaction and the aldehyde part would be the most electrophilic but it doesn't get the right product unless there is an additional step. I think it might be an aldol then rearrangement
Exaclty. I didnt want to just give you the answer. Try to draw the aldol and figure out the rearrangement :) I think youre on a good way

Offline confusedug45

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Re: Enolate chemistry
« Reply #4 on: May 20, 2020, 08:23:38 AM »
I got the second step, it's just intramolecular nucleophilic attack from the O, followed by tautomerisation and then an e1cb. Still no luck with first step. I know it involves an aldol but could you give me a hint as to what else? or where the aldol attacks?

Offline rolnor

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Re: Enolate chemistry
« Reply #5 on: May 20, 2020, 10:36:00 AM »
It must be a acetylation-step also? Or does the acetyl migrate?

Offline confusedug45

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Re: Enolate chemistry
« Reply #6 on: May 20, 2020, 12:00:01 PM »
I've figured it out, thank you for the help.

Offline kriggy

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Re: Enolate chemistry
« Reply #7 on: May 21, 2020, 03:00:36 AM »
I've figured it out, thank you for the help.

Can you show us? Maybe someone else in the fufuture might be interested in smiliar kind of problem

Offline confusedug45

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Re: Enolate chemistry
« Reply #8 on: May 24, 2020, 07:19:38 AM »
Yeah sure

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