September 25, 2023, 10:30:52 PM
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Topic: Alternative solvent to Glycol/Diethyleneglycol for Wolff-Kishner Reduction  (Read 2762 times)

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Offline zuriel

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I'm doing a reduction on a 7-Azaindole-3-oxoacetic acid. Normally with indoles you can acidify to pH 2 and the acid crashes out of solution but in the case of 7-Azaindole nothing crashes out so you need to acidify to pH 5 and extract with EtOAc.

Only problem here is that some of the high boiling solvent gets carried through. I've tried extensive water washes to remove as much as I possibly can but it still remains in the NMR spectrum.

I know I can use the K├╝gelrohr or possibly columning the acid but since I'd rather avoid both of these if it's at all possible.

Does anyone have any other suggestions as to what solvents I can try? Someone suggested Dioxane as it's more easily removed - I just want to hear any other suggestions before I go trying that.

Thanks everyone!  :)

Offline opsomath

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Re: Alternative solvent to Glycol/Diethyleneglycol for Wolff-Kishner Reduction
« Reply #1 on: February 22, 2014, 10:21:21 AM »
Sorry to be Captain Obvious, but have you checked out the references for the Wikipedia page on the WKR? There are some versions that run in other solvents which would be easier to get rid of.

http://en.wikipedia.org/wiki/Wolff%E2%80%93Kishner_reduction#Modifications

Offline zuriel

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Re: Alternative solvent to Glycol/Diethyleneglycol for Wolff-Kishner Reduction
« Reply #2 on: February 22, 2014, 10:27:16 AM »
Sorry to be Captain Obvious, but have you checked out the references for the Wikipedia page on the WKR? There are some versions that run in other solvents which would be easier to get rid of.

http://en.wikipedia.org/wiki/Wolff%E2%80%93Kishner_reduction#Modifications

D'oh. I should have thought of this myself - thanks for being captain obvious - any help is appreciated like I said. I might try the Toluene one!  :)

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