reacting Lysergic Acid with Ethyl Trifluoromethanesulfonate

[Flufferus]

I hope this is ok for me to post. if its not please remove.

I will be reacting Lysergic Acid with

Ethyl trifluoromethanesulfonate.

I will be doing this in dry ice with acetone, looking to achieve esterfercation under -78c conditions.

1.O-alkylation: The ethyl group attaches to the oxygen, creating ethyl lysergate.
2.this will then undergo aminolysis, back to an amide via diethylamide.
3.**Interesting thing**


If it goes wrong, i will end up with a resulting compound with a quaternary ammonium ester salt.
To be more precise, it would be the ethyl ester of N-ethyl-lysergic ammonium triflate.
should i not do this under extreme low temperatures.

Hopefully the resulting product is interesting.

Proper PPE will be used of course.

 

[Flufferus]

plans have changed. i will be making a unique compound, i will still be undergoing O-Alkylation, but in addition, i will also be preforming N-Alkylation.

1. Double alkylation: The reagent attacks both the oxygen and the nitrogen on the same molecule.
2. I will then react this new molecule with diethyl, producing.... something. I am hoping to have a unique compound. I will hopefully achieve comparable potency to regular plain EL. As if i had only done the O-alkylation, but with this new "structure" added.

3.

N-alkylation: The ethyl group attaches to the nitrogen, creating the quaternary ammonium salt.
O-alkylation: The ethyl group attaches to the oxygen, creating ethyl lysergate.

1. This new double alkylated molecule will then undergo having an amide added to it, creating a quaternary ammonium ester salt.
2. ethyl ester of N-ethyl-lysergic ammonium triflate -----> Diethyl,amide -----> ??????

Hoping the ?????? is interesting compound....