Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: confusedug45 on May 18, 2020, 10:50:57 AM
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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.
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What about aldol reaction?
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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
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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
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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?
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It must be a acetylation-step also? Or does the acetyl migrate?
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I've figured it out, thank you for the help.
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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
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Yeah sure