September 23, 2019, 07:32:37 AM
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Topic: How do you make all of the SM react in a solvent free reaction?  (Read 904 times)

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Offline OrganicDan96

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Re: How do you make all of the SM react in a solvent free reaction?
« Reply #15 on: May 21, 2019, 05:22:31 PM »
DMAP is actually a terrific base for aminations, but probably not necessary here.
its not just abase but an activator as it's nucleophillic

Offline wildfyr

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Re: How do you make all of the SM react in a solvent free reaction?
« Reply #16 on: May 21, 2019, 06:06:40 PM »
DMAP is actually a terrific base for aminations***, but probably not necessary here.
its not just abase but an activator as it's nucleophillic

Completely true, it creates a transient activated ester, as in DCC/DMAP amidation.


**this should say amidation, not amination.

Offline rolnor

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Re: How do you make all of the SM react in a solvent free reaction?
« Reply #17 on: May 22, 2019, 03:59:04 PM »
You get a acylpyridinium ion, pyridine is similar as DMAP.
« Last Edit: May 22, 2019, 05:41:07 PM by rolnor »

Offline wildfyr

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Re: How do you make all of the SM react in a solvent free reaction?
« Reply #18 on: May 22, 2019, 06:59:40 PM »
DMAP is a better nucleophile than plain pyridine. Also it doesn't stink as bad and is often used in subequimolar amounts. .

Quick tip for anyone trying to remove pyridine or other pyridine like molecules from a reaction that is acid sensitive: copper sulfate extraction.

Offline hypervalent_iodine

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Re: How do you make all of the SM react in a solvent free reaction?
« Reply #19 on: May 23, 2019, 12:49:17 AM »
DMAP is a better nucleophile than plain pyridine. Also it doesn't stink as bad and is often used in subequimolar amounts. .

Quick tip for anyone trying to remove pyridine or other pyridine like molecules from a reaction that is acid sensitive: copper sulfate extraction.

Could not recommend this enough. Some of my more difficult amidations using pyridine went from ~40% to ~85% yield just by changing the work up to 1M CuSO4.

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