Eureka!!

After the 5th time...i think...trying to separate my cpd...i finally figured the 2 spots on my TLC is due to the 2 E/Z isomers of my compound!!

Well all this while the NMR and MS results seem to indicate that the cpd I wanted is in all fraction...but I thought it's just because the other cpd I can't identify has similar NMR spectra :P

Hmm...but I still can't figure out y the isomers of my cpd appears as 2 totally different spots on TLC..
...and still can't figure out why it can't be separated if they r 2 different spots...

Maybe my cpd isomerize in solution..so even though it was initially one isomer when it came out from the column...but by the time I spot it on TLC...it has become a racemic mixture??

Dunno lah...anyway, doesn't matter which isomer...it's just an intermediate (oxime) which will be converted into a non-chiral cpd (primary amine)...so who cares which isomer it is...
So I just wasted a lot of time...and plenty plenty solvent and columns...wahaha...

Time to move on :D