Decarboxylation of tryptophane using...

[Stanley]

What about using MDP2P as the ketone catalyst when decarboxylating tryptophane?

It has a very high boiling point (253 °C?), and is IIRC very susceptible to imin formation  

Using naphtalene as the solvent, it oughta be the ideal decarboxylating system. And no reflux is necessary, since one doesn't have to heat it above 200 °C (however one might not want to have gaseous naphtalene in the lab, so a fume hood might be a good idea).

Considering the amount of ketone needed it's almost economically acceptable as well  


Stanley

[Sunlight]

There's a post in wich plain DMF is used and seem to work satisfatorily. Better use that ketone for other things.

[hest]

My eksp. with high boiling ketones (ethyl,hexyl-keton ect.) is bad.

[Stanley]

Why are high boiling ketones bad?

[hest]

Course the yeald was low.

[Vitus_Verdegast]

There are thousands of high-boiling ketones to be found *everywhere*, so maybe a substance like MDP2P has better usages, don't you think...  

A low yield was obtained by using DMSO ; DMSO/Cu-chelate ; DMSO/acetone and turpentine/dill oil. I thought the latter was the most promising, after Student's research, but since L-Trp is completely insoluble in the hot turp you need to have really good stirring, especially when working with larger amounts, or this reaction is going to take days.

My dill oil (french seed oil) contains 40% carvone. Maybe DMSO/carvone would be better (solubility) ?

"There are many things under the sun."