April 19, 2024, 11:54:24 PM
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Topic: Grignard Addition to Anhydride  (Read 3694 times)

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Offline rolnor

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Re: Grignard Addition to Anhydride
« Reply #15 on: March 14, 2019, 02:39:06 PM »
Have you done searching online like scifinder for the aldehyde? Its a simple startingmaterial. I think the amide with the carboxylic acid you are making could be tricky to handle, hydrophilic. Also the Grignard will quench with the acid, I guess you will take excess of the Grignard?

Offline AlphaScent

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Re: Grignard Addition to Anhydride
« Reply #16 on: March 14, 2019, 03:07:58 PM »
The reference gives 96% yield.  I am not too worried about the hydrophilicity.  I will be using 2 eq. of Grignard.
If you're not part of the solution, then you're part of the precipitate

Offline AlphaScent

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Re: Grignard Addition to Anhydride
« Reply #17 on: March 19, 2019, 10:01:35 AM »
Spirochete gets the ball with 2 seconds left...puts it up!!!! ITs GOOD!!  The crowd goes wild!!!

Weinreb amide from anhydride was made cleanly in 93% yield.  Subsequent treatment with 2.5 eq of isopropenylmagnesium bromide in THF (0.1 M reaction solution) at RT gave the desired product in 86% yield.

Thanks Spirochete!!  Please DM me your info.  I will DM you mine. Want to put it in my NB for an acknowledgment when I eventually write the paper.

C13 NMR of product: 200.9, 178.3, 144.7, 124.83, 43.6, 40.7, 26.8, 20.0, 17.5

Quite clean even before any purification.  I will tackle that once I return from golfing in Myrtle Beach. 

Thanks again Spirochete and all who offered ideas!

Cheers!
If you're not part of the solution, then you're part of the precipitate

Offline rolnor

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Re: Grignard Addition to Anhydride
« Reply #18 on: March 19, 2019, 10:08:16 AM »
Great!

Offline wildfyr

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Re: Grignard Addition to Anhydride
« Reply #19 on: March 19, 2019, 10:08:52 AM »
Makes me warm and fuzzy inside

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