[Sevigny86]

Hey everyone,

Firstly I'd like to mention I work with heteroaromatic sulfinate salts which have quite a scarce amount of literature. I recently have developed a method in synthesizing these sulfinates with the use of TMEDA which basically prevents contamination of my salt with other organic/inorganic impurities. However, I was wondering if there was a simple way I could remove TMEDA from my product (Lithium Benzofuran-2-sulfinate) such as rinsing or forming an azeotrope. I've searched quickly and haven't come up with anything significant, wondering if any of you have ideas.

Thanks in advance!

[Doc Oc]

Typically tertiary amines are washed out with a mild aqueous acid (1M HCl is most common).  This actually sounds ideal for your compound because the sulfinate salt will just protonate in acidic solution and then partition into organic media.  So if you take up your crude mix in 1M HCl and then extract that mix with ether or ethyl acetate you should get the sulfinic acid and the TMEDA will stay in the aqueous.

[Sevigny86]

Thanks for the reply!

One of the issues with sulfinic acids/sulfinate salts and the reason why little research has been done on them is partially due to their instability in their protonated, sulfinic acid form. They often decompose or oxidize very easily, therefore I need to store them as salts. Although I'll definitely try that, I was wondering if any other method would be possible..

[Sevigny86]

I found that thorough washings with a large amount of THF removes the TMEDA coordinated to the sulfinate. Thanks for the *delete me*

Thanks for the *delete me*

[Sevigny86]

Soxhlet with THF has removed all traces of TMEDA*