Chemical Forums
Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Humr on November 16, 2020, 04:05:42 AM
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Hello. I would like to ask if someone has idea what to use instead of tert-Butyl hydroperoxide in this reaction. I work with betuline and i cannot use peroxides because epoxide between C20 and C29 would form.
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What reaction do you want to do with betuline?
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I want to have COOH on C30. I do this reaction only with SeO2 in glym. It does alhehyde on C30. I would be glad if i could skip second oxidation.
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Have checked Scifinder or Reaxys? It seems this should be possible to solve.
Here is a link, they use t-BuOOH but dont get epoxidation?
One more thing; If you do get epoxide you can convert it back to alkene with PPh3.
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Betuline is what i want to use. Reaction below is what i found in some literature. That is interesting idea. So are you suggesting to use SeO2, T-BuOOH and PPh3 at once?
I have some idea too. How i normally do this reaction is: Disolve betuline in 2-metoxyethanol, add 2 eq. SeO2 and reflux for 4h.
What if i add Fehling's solution to this reaction?
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No, if you get epoxide you isolate this and treat with PPh3.
I think its better to include oxidation of the aldehyde as avseparate step, there are manyways to do this and yields should be high.