We will sometimes do DCM to EtOAc gradient for hard to dissolve compounds. But more mixed waste, so not ideal.
If very polar, supercritial fluid chrom. works wonders, I just used it for some compounds that are quite polar and hard to do on silica, but on SFC, the compounds gave sharp peaks, good separations of similar materials, and high loading using 0 to 20% EtOH in CO2. Very hard to get any purification on silica, but got 100 mg at a time done in 10 minutes on SFC with a semi-prep column. Just have to find someone with a system, but becoming very popular now.
Plus you can drink the organic waste. :-)