Try, try again. And again. And again. And again…

Well, my project for my synthesis class is, apparently, hopelessly doomed. My compatriots and I working on the chiral auxiliary project have hit the same wall as students last year did (confirmed by our TA), the attachment and removal of the auxiliary. I coincidentally happen to be up to my eyeballs in pseudoephedrine, which, (for any over eager readers) is not as fun as it sounds: rather than reduce the stuff and sell it on the streets, it’s already been earmarked (condemned) to reactions with propionic anhydride. That reaction’s just fine, but it’s the propionamide’s fate in the Sysiphus-like auxiliary attachment/detachment that’s causing problems…

Anyway, apparently the conditions achievable through our methods are simply not stringent enough for the reaction to work in an efficient and repeatable manner. Therefore, given that there’s no clear end in sight and we’ll never get off this stupid island so there’s no use trying, lab periods have become less and less about the destination, and more and more about trying to forge new paths to get there. None of them have worked so far, but it’s all about the learning experience, right?

Now, everything’s kind of turned into a contest for “style points” and lab is less of a “lab” period, and more a “chemistry jam session.” Who has the best ghetto-rigged solutions for specific apparatus? Who has the best looking columns/best way of “automating” a manual column? Who’s got the prettiest lookin’ NMRs and best tricks to get it that way?¹ For the steps that we’ve obtained good (‘publishable’ for final paper) results, we’ve begun to divide and conquer epic scale-ups so that we can have ammunition readily available to conquer the next step.

For the latest step, and/or extra steps, we’re starting to try new methods – not necessarily to get results, more to get exposed to new techniques. A little while back I spent the better part of a lab period attempting to vacuum distill the propionic anhydride to hopefully boost the yields on the pseudoephedrine reaction. It was completely unnecessary within the scope of the project, but still worth a shot. Did it work? Nope. At some point during each attempt, a disgusting bump occurred, shooting impure garbage (and disgusting, blackened phosphorous pentoxide drying agent) through the short-path, causing an epic re-start. Worse than that, the yields went up and matched published yields as soon as I scaled up the reaction, anyway. But it’s cool – I wouldn’t have encountered a vacuum distillation otherwise during the course. And, aside from using iffy drying agents that turn my solution weird colors, I’m pretty confident I could properly pull off a proper vacuum distillation on my own, without having to look up a procedure of any sort. (So, it’s not rocket science, but for extra pure stuff, I would have had no idea to flame dry the glassware.) While the grizzled/jaded vets out there can attest, its nothing to throw a party about, I still think it’s pretty cool that I picked up something that nobody else has really encountered in lab yet, and even if peers are doing actual research, depending on the research environment, it’s still something they might not come across for a while.

Ultimately, I’m not blazing any trails that fellow chemists haven’t been walking for some time now. However, it feels amazing to ‘play’/explore, something that’s not really encouraged in the research lab, and something that teaching labs haven’t let us do so far.

Perhaps you’re not a chemist, or if you are, maybe you’ve lost the feeling of when something like running a vacuum distillation was fun, new, or exciting. So, best I can liken the overall experience to is taking a vacation to a city you don’t know, and learning how to navigate it while you’re there. At first, you probably know where your hotel is, and little else. You start to explore, learn where a few major streets are, and start to forge deeper and deeper into uncharted (to you) territory. Wrong turns aren’t necessarily bad; they’re usually fun, and still give you insight to the city that you previously didn’t have. Depending on the layout of the city, and if you’re good/lucky, you might even start to navigate instinctively, based on where things should naturally be with respect to your mental ‘working model’ of the city. It’s like that.

That doesn’t sound like a vacation to you? Then you’re just no fun…

[1]Speaking of NMR tricks, I shared the No-D NMR technique, and got looks of “your crazy… so crazy it just might work.” Thus far, we haven’t needed to titrate butyllithium, but I think I might, just to blow their minds.


2 Responses to Try, try again. And again. And again. And again…

  1. George says:

    Nice Blog! I am impressed how bad-ass you are!!

  2. […] mentioned before, the synthesis class hit a brick wall when the use of a chiral auxiliary simply failed to work. […]

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