Just a Suggestion
by Jeremy on Jun 20 2008 (1647 Views)
Picture this: you are expected to do a cross-metathesis, Mitsunobu, hydrolize the ensuing ester and cross-couple with (s)-proline. Not necessarily a difficult order to an experienced organic chemist. The challenge is finding a procedure/reference that will work on your substrate. You crawl through several Google searches (because you’re too lazy to get to walk across campus to the library and use SciFinder) and come up with ballpark, unreasonable hits. Are you seriously going to do a cross-metathesis in cresol just because the paper says there was a “noted rate enhancement”? How many total syntheses will you crawl through to find the right tosylation procedure? I encounter this frustrating problem on a weekly basis. Isn’t there a middle of the road procedure or set of procedures someone can consult?
Look no further than Li, Limberakis and Pflum’s relatively recent book entitled Modern Organic Synthesis in the Laboratory (ISBN-13: 978-0195187991). Truthfully, I’m not one for plugging media (movies, music, books, etc.), but this text rocks! It’s on par with Li’s Named Reactions (ISBN-13: 978-3540300304) book, which got me through cumes a few years back.
Those who know me well also know that I’m obsessed with Leonard, Lygo and Proctor’s Advanced Practical Organic Chemistry (ISBN-13: 978-0748740710)—a splendid reference covering the ins and outs of any organic laboratory. It’s full of useful information ranging from how to set up a laboratory notebook to Grignard preparation to anoxic techniques. I’m living proof that any idiot can consult APOC and have a vague idea of how to correctly conduct a majority of laboratory techniques.
Similarly, Li’s MOS puts a modern twist on most of what APOC covers then throws in generic procedures for running a cross-metathesis or doing a EDCI-mediated peptide coupling, for example. There’s even a section on lab coats! (SPOILER ALERT: baggy is not the way to go). My only criticism is that I wish there were even more information. Though, both references are conveniently concise (~200 pages) and cut through the BS that most technique books love to cover.
My boss received a desk copy of MOS a few months back, and I think it’s spent more time on my desk than his; I just added the book to my Amazon wishlist. I encourage you to do the same (even all you nuclear chemists…you never know).
Wow, that looks useful! I can Scifinder like my life depends on it, and can get most published procedures to work reasonably well unless they hate my substrate, but when there ISN’T something to follow…I’m lost. Ordering a copy. Hopefully it will help.
Great suggestions! This is something I have struggled with a lot as well . . . efficiency vs. practicability. I would add that one excellent free reference is the Organic Synthesis website, and one not-so-free reference that is steeped in trie-and-true methods for classical organic synthesis is Vogel’s Practical Organic Chemistry.
Jared
As long as I’ve got funding, I go for practicability every day. I’m working for a cleaning products company and I have to experiment with different cleaning chemicals to come up with the next “best” cleaning product. Part time I lecture at Stony Brook to graduate students, and I teach students that in the real world, you have to either produce results or depending on where you work, you can save the company or organization you work for money by not taking too many risks when conducting experiments.
I never had the chance to use Vogel before, though I own a copy of (I think) the second edition (published ~1940). I’ll have to add the 5th edition to my Amazon wishlist, too.
Orgsyn is pretty helpful too, but I often struggle to find the right procedure I need. In addition, I wish Orgsyn would redesign their website and/or get rid of the survey they’ve been running forever.