So i tried hydrogenation with hydrogen and Pd/C in ethanol. I observed zero conversion.
Montmorilonite works. It reacts at the room temperature. This reaction is also dependent on solvent.
I observed full conversion of starting compound only in acetic acid. Unfortunatelly i can see on TLC 2 spots with almost identical RF. It looks like one is shadowing another.
In DCM there is only partial conversion, some another sideproduct and shadowing.
In methanol there are at least 4 products.
THF and DMF provide very low conversion of starting compound.
Toluene provides one sideproduct, no shadowing and quite satisfactory conversion of starting compound.
So i am considering to work up toluene reaction mixture and analyse it, since it is best result i have.
Rolnor, do you use 90% HOAc on this compound, or something else? And can i ask you for exact conditions, please?