Now we're getting somewhere but not with the oxidation

21 Sep
Published by pylioja

Subject 

Miscellaneous

Ok now I'm getting close to TCMDC-123812/123794. A slight change of tack for the alternative core synthesis seems to have paid off. First alkylation of ethyl acetoacetate with chloroacetone and then condensation with 4-fluoroaniline appears to have given the pyrrole with an ester on the 3-position quite nicely in 61% yield over the two steps after recrystallisation (PMY 8-1). Sometimes it just pays to change the plan completely when you feel like progress is slow.
Reaction Scheme
I still want to get that oxidation to work. I think I'll head down the periodic acid alley next but for the moment I'll use the ester. It's quite a bit nicer anyway.

Comments

MatTodd's picture

Fantastic. That final TLC you have here is a thing of beauty. You didn't colour it in with a red pen, right?