Some normal phase column chromatography for y'all. We love colored fluorescent compounds! Fuck trying to see where your shit is on a column if it's white or colorless. I also love that I can just shine a UV lamp on the column to find my compound and it'll glow.
Anyway, I'm running it in pure methanol (very polar) and probably eluting some of the silica gel filling the column (polar). This is a pretty wild column to run (but we're doing it anyway because it's what folks did in the literature), since you should use a (relatively) nonpolar mobile phase (like dichloromethane or hexane) with a polar stationary phase (silica powder/gel) to get the (relatively) nonpolar compound off, buuuuuuuut my compound is slightly polar. And it's stuck (this pic is from loading the column but I've run the column w liters of solvent and there's still a distinct stripe that is not moving) and I have precious little of it to fuck around with troubleshooting and transferring around. Like yield is definitely less than 50mg /total/ bro. Like I spent a summer painstakingly making all the precursors that led to this. Like I'm so fucked if I lose any more of it.
What I should do in the future is get reverse phase columns (polar mobile phase, greasy nonpolar stationary phase) so my compound is less likely to get stuck and comes out faster, BUT they're fucking expensive ($$$) and would take forever (like 2-4 weeks) to receive if I ordered them (supply chain issues). :(
So I'm drying the column out and I'm going to tip it upside down and let the sand and silica come out into a round bottom or something and resolvate with methanol and just try and filter it and hope only my product precipitates and all the junk flows through.
