Super Psyched

My best friend keeps complaining to me that I sound like a "surfer" all the time when I tell her how "stoked" or "psyched" I am about climbing. In this case, Proper English will have to yield to unbridled youthful exuberance. I went up to Cathedral yesterday with Neal. I had heard various moanings and groanings from others about how wet and unpleasant it was going to be, but a 20% probability of precipitation is not to be passed up in this rainy season that is passing as July. In truth, things were wet, drying out halfheartedly, and most importantly, climbable. I led Still in Saigon (5.8) which I had done a few years ago with Kevin Mahoney, but remembered nothing about. It was my hardest trad lead so far, but I felt good about it. There were definitely a few dicey slab moves on it, but my time working the 5.11 slab on Gunboat Diplomacy and my many self-taught slab lessons at Metrorock have paid off, because I feel reasonably good on slab these days. Then we ventured over to Recompense (5.7), and while the upper pitches were wet, the first pitch was fine, and Neal led that. I think that was his first time with double ropes, and it was an educational experience for him. He got a bit off route, but with the help of the doubles and a lot of extended slings, he managed to salvage the off-route choss-pile into an overall route. In other words, he made it work with what he had, which I think is a really important skill.

We ran into the redoubtable Bayard Russell at that point, and they ran up the first two pitches of the Prow, so I went over to investigate. As it turns out, there's an easy variation and a standard 5.10a variation, so I chose to do the 5.10a version. It's a slabby thing with a few cam placements and a few bolts, so it felt very reasonable. I felt a little scared going over the crux, but my head is really in a much better place these days, and I just went for it and did fine. I took a look at the rest of the route, and it looked awesome.

[Advertisement. I want to go back and aid the route so I work parts of it. Eventually, I want to free it. Who wants to learn how to do some simple aid climbing and jugging? Let me know if you're interested! The route is A1 or A2 with a lot of fixed protection and goes free at 5.11d. You don't need to be able to climb harder than, say, 5.9, but you do need to be good with gear, very patient, and even more psyched.]

Neal finished off by doing some sort of very wet, scary crack at the North End. I didn't catch the name of it, but there were some exciting shenanigans required to clean the damn route. Today was brutally wet. It rained a lot. I tried to convince Dunbar, Jimmy, Alon, and Jim to climb at Sundown with Neal and I, but we were passed over. They did show us a cool little campsite though. Instead, we climbed with various North Conway Cool People like Freddie Wilkinson and Janet Bergman, who are to us as, say, a five course meal is to one of those oily rags which passes for burgers at Burger King. We got on Eyeless. Neal did quite well, while I flailed about ineffectually. Everything felt really greasy.

Driving home, we passed the exciting exit number of 26 on I-93 and I thought we'd go and check out Flesh for Lulu again, as the sun was poking its head from out of the clouds in an encouraging, but desultory fashion. Neal got on, and made good progress, but seemed to find it harder than Eyeless (12b), even though it's apparently graded easier (12a/b). But whatever--who cares? We had a great time. I got one good burn in. At the crux, you get this core-wrenching left hand gaston crimp (which is somewhat sharp and gave me a blood blister last week), hike your feet up, and dynamically (if you're me) or statically (if you're good, or maybe just tall) go up to this jug. Everybody uses this really high right foot that looks like someone's bottom lip, but I discovered today that the dyno was way easier if I used a foot that was closer in. Or maybe I was just feeling stoked. Who knows? I made a full on dyno and stuck it first try, which I felt great about. I shook out and traversed up to the final boulder problem, and blew one of the final moves before the last bolt is clipped. So that was, by far, my best burn on a 12 so far, so I'm really excited about that. I think it will actually go soon, just as soon as I get a little more endurance. I did feel slightly scared doing the last boulder problem, since I was so pumped, and as I deadpointed to this good three-finger sloper/jug thing, I felt my concentration wander slightly, and I missed it. I think this shows how important mental conditioning is. I probably haven't improved physically that much since last week, but I rehearsed the crux sequence in my head a million times this week, and when I went to do it, it felt great. The last boulder problem, however, I didn't really think that much about, and as a result, when I got up there, it was weird and I had to think, which was bad, because I was already super pumped. And being super psyched and unafraid really helped--I find I can never climb effectively if I'm worried my belayer is going to unexpectedly dirt me...

Well. I'm back to the lab. My complicated substrate synthesis is being delayed at present not just by all the climbing, but also by a lack of material. I'm spending a lot of time bringing up material and making reagents. I just made the beta-acylphosphonate reagent for installing E alpha, beta-unsaturated 2-oxazolidinones via Horner-Wadsworth-Emmons reactions, and it was brutal. First, you take the sodium amide resulting from the reaction between 2-oxazolidinone and sodium hydride, and acylate it with bromacetyl bromide. That works pretty well, and much better, I've found, than going with n-butyllithium. Then you treat it in an Arbusov reaction with trimethyl phosphite. Unfortunately, this generates a load of highly toxic bromomethane gas, which also has the effect of creating the undesired side product of methyl dimethyl phosphonate. This has to be distilled off, and the resulting nasty red-orange oil crystallized into the desired phosphonate, a nice white crystal. Well, while the NMR spectrum looked fine, it just refused to crystallize, so I was forced to run some flash chromatography in methanol/dichloromethane, which is definitely one of my least favorite solvent systems. I put my nice yellow solution on the rotovap, and went to the bathroom, and when I came back, I found that someone (probably me) had accidentally brushed up against the rotovap, and it was now at an undesirably toasty 70 celsius. Oooops. And now I had a red-orange oil again. But luckily for me, the whole thing started to crash out very slowly over the next few hours. So I'm stoked about that, too. Next up is allyl diazoacetate, which I've never been able to make very well, and may try to figure out. Something about the deacylation of the intermediate beta-keto, alpha-diazo allyl ester never seems to go according to plan.