pyridine

The ligand that I've been working on (the A+B = C+D thing in a previous post) has been one tough cookie to crumble. The main reason for this is (I think) that the solubility of the starting material is pretty poor in THF, which is the solvent of choice for analogues of the target compound. The smart move here is to switch to a better solvent. After testing solubility of the starting material in a number of different solvents (THF, fluorobenzene, nitromethane, glyme, pyridine, DMSO, and methylene chloride) it turns out that this stuff is soluble only in pyridine and DMSO. DMSO is a great solvent if you never want to isolate your product again. Everything is soluble in DMSO. I'm soluble in DMSO. It boils somewhere up around 180C which doesn't really make it strippable. This leaves pyridine, which is what I've been using, but I can't say I'm terribly excited about this either. It stinks(if you can smell it, you're not working carefully enough), its tough to dry, tough to vacuum transfer and is particular bad for gentlemen such as myself, if you know what I mean. (For those that don't know, pyridine could be used as a very effective male sterilizer, so long as you don't mind not having lungs, a liver, or several other major organs as well.) The upshot of all this is that when I get frustrated trying to get the pyridine to pump over in time for me to get down to my NMR time, I can't throw the bomb to the floor in frustration for consideration of my future kin.