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Topic: Grignard Reagent with CH3I and diethyl ether  (Read 2912 times)

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Offline Puchini 101

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Grignard Reagent with CH3I and diethyl ether
« on: June 07, 2016, 02:26:52 PM »
Does anyone know why Grignard reagent of CH3I can only be prepared using diethyl ether as a solvent and yields no reaction when developed in THF?

Offline orthoformate

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Re: Grignard Reagent with CH3I and diethyl ether
« Reply #1 on: June 08, 2016, 12:11:26 AM »
Does anyone know why Grignard reagent of CH3I can only be prepared using diethyl ether as a solvent and yields no reaction when developed in THF?

I think that magnesium degrades the THF. I looked all over for a reference, but I couldn't find one.

Offline clarkstill

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Re: Grignard Reagent with CH3I and diethyl ether
« Reply #2 on: June 08, 2016, 04:08:25 AM »
Does anyone know why Grignard reagent of CH3I can only be prepared using diethyl ether as a solvent and yields no reaction when developed in THF?

I don't think this is true. A reaxys gives quite a few hits for formation of MeMgI in THF although Et2O seems to be more common, for example:

http://pubs.acs.org/doi/suppl/10.1021/jo052418r

In general I think it's easier to get a hold of dry Et2O and less risk of contamination with peroxides etc., so quenching of the grignard by water or unwanted side reactions will be easier to avoid.

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