Just starting my research PhD now and loving it so far.
Currently trying to get this reaction to work though.
I want to form the oxoacetic acid derivative of 7-azaindole. So far I know that I need to dissolve the 7-aza in diethyl ether react it with glyoxyl carbonate. It's the next part I'm having trouble with though.
Following a colleague's thesis - his method of preparation of the oxoacetic acid derivative of 7-aza with a METHYL group on the 1 position involves first forming the acid chloride of the 1-methyl-7-azaindole then removing the diethyl ether under reduced pressure - suspending the crude in acetone and adding an aqueous KOH soln. This is left stir at RT for 14 hours and then acidified to pH 2 using HCl (aq) to give the oxoacetic acid which crashes out as a white ppt.
I'm wondering should I just use a milder base in the case of 7-azaindole being my starting material? So far everything is good up until I acidify the crude mix and there's no ppt. I haven't gotten an NMR of my crude yet but I have a gut feeling it went wrong somewhere.
Any suggestions would be appreciated! Thanks!
PS- writing this in a hurry so if you have any questions/need clarifications please ask.