We attempted a column on a similar compound this week. It dissolved easily into DCM, but when we began to develop the column in 50:50 ethyl acetate/hexanes, the material became crystalline and started to poke up through the sand layer at the top of the column. Because of the possibility of streaking due to insolubility, we decided to switch to 100% ethyl acetate and accept that the separation would not be as good as one could imagine. Again, we saw crystals in the fractions with the greatest amount of materials. I am contemplating the synthesis of a third compound that would be similar to the other two. Either we would either try to recrystallize it, or we will use a different solvent system entirely, probably one based on DCM or chloroform.