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Topic: Grignard Reagents and Alcohol  (Read 1997 times)

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Offline Cooper

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Grignard Reagents and Alcohol
« on: January 08, 2013, 08:20:52 PM »
Hi,

I am synthesizing a molecule on paper and I am adding an alkyllithium to a molecule that has an epoxide and an alcohol. I am hoping it will open the epoxide, is it possible that it could deprotonate the alcohol?
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Offline discodermolide

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Re: Grignard Reagents and Alcohol
« Reply #1 on: January 08, 2013, 08:23:11 PM »
You will need either to use 2 equivalents of your lithium reagent of protect the alcohol because it will react with the alcohol preferentially. So protect the alcohol.

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Offline Cooper

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Re: Grignard Reagents and Alcohol
« Reply #2 on: January 08, 2013, 08:25:41 PM »
Hm, not what I wanted to hear, but thank you. Will the stereochemistry be preserved if the epoxide opened?
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Offline discodermolide

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Re: Grignard Reagents and Alcohol
« Reply #3 on: January 08, 2013, 08:28:03 PM »
Should be, yes.
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Offline Cooper

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Re: Grignard Reagents and Alcohol
« Reply #4 on: January 08, 2013, 09:41:31 PM »
Thanks for your help. :)
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