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Author Topic: Question on the oxidation of ethers  (Read 69 times)

Naphyrone

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Question on the oxidation of ethers
« on: December 23, 2012, 12:26:04 AM »
I've been contemplating an idea, forming the isopropyl ester of alanine, reducing it leaving an ether and then oxidizing it, however I am curious as to what products I would be left with post oxidation using KMnO4. My hopes are sec-butylamine and isopropanol/acetone.

Ferrum

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Re: Question on the oxidation of ethers
« Reply #1 on: December 30, 2012, 08:08:57 AM »
You are planning on treating the isopropyl ether of alanine (with its carbonyl oxygen removed) with KMnO4 to yield sec-Butylamine?

I believe it would oxidize to an ester, but maybe I'm incorrectly reading what you want to attempt. Just in case, this would probably be run in DCM with a ptc.

Also possible but unlikely I think is the potassium becoming coordinated with multiple oxygens from multiple isopropyl alanine ether molecules.

FYI sec-Butylamine can be found otc

atara

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Re: Question on the oxidation of ethers
« Reply #2 on: January 04, 2013, 06:25:28 PM »
KMnO4 will oxidize a primary amine... I don't even know if you can reduce an ester to an ether in the first place. Usually reducing an ester cleaves it, because it proceeds through the hemiacetal.

If sec-butylamine is what you're after, I suggest a Leuckart reaction on butanone, or, as Ferrum suggests, simply purchase some.
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