Canyon Ishikawa, Organic Chemistry at Scripps Research Institute, Week 6

Posted in: Pinhead Intern Blogs, Canyon Ishikawa, 2022 Interns
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The sixth week of my internship felt surreal the entire time. As I processed these were probably the last days I would be doing these things and living in this area, I tried to live it up and take on each and every task that I could. Other than that though, this week was filled with a lot more work under Johny and honing my craft in organic chemistry that I’ve learned over the past 5 weeks. It was bittersweet as I felt the greatest amount of independence in the lab, but knew I would be leaving at the end.

 

Monday started off with me and Johny going around the building  to find chemicals we needed that weren’t in our lab. Johny had emailed all these separate people prior to this, so we knew who had what and could go directly to them instead of having to ask each and every lab. Once we had everything we needed, we were able to set up three reactions. I then TLC’d them throughout the day to see how complete each one was. Eventually we could see that one of them was fully reacted, so I ran an aqueous workup on it to neutralize it and purify it out. This consisted of adding water and Ethyl Acetate to the reaction and putting it into a separatory funnel, so I could then separate the organic material from the water and other substances due to their different densities.

Tuesday began with me TLC’ing the two reactions that we left running overnight. One of the reactions was complete, so we ran another aqueous work up on that. This time I used sodium bicarbonate and dichloromethane for the work up. I then rotovapped this material down so we could get a pure substance. I then loaded this substance into a biotage cartridge so that we could biotage it, because we still saw multiple molecules within the substance instead of the pure molecule that we wanted. Once the biotage was complete, I TLC’d the vials to see where the different molecules were in separation. I then spent the rest of the day rotovapping the different sections.

 

Wednesday was a pretty loaded day. I began TLC-ing reactions that Johny had set up the previous day at different gradients of solutions (hexanes to ethyl acetate). This showed us the different separations that each gradient gives us so that we know what gradient we should run our biotage at. Once we found the right gradient, 40% Ethyl Acetate – 60% Hexanes, we ran  aqueous work ups on them and rotovapped them down to get pure substances. We were then able to load the materials into biotage cartridges and run them. After this was done it was lunch time and Keary, the lab manager, took me out to eat at this nice spot. After we got back I TlC’d the vials from the biotage and rotovapped them down. The day then ended with me and Johny NMR’ing the different sample we got from the biotage. Unfortunately, none of them were what we wanted.

On Thursday, I started the day by running an aqueous workup on a reaction Johny had set up the prior day. This was with water and methanol. I then hand columned the substance from this. A hand column is what biotage does, but by hand instead of machine. This allowed us to preserve the silica with a base, as the silica is partially acidic and our material is very sensitive to acids. This took up the entirety of the day.

 

Friday was a super slow day. Johny needed to work on his presentation for the group meeting and we were basically done with all the actual chemistry stuff we had, so it was a lot of waiting around. Eventually a group meeting came around and I watched Johny’s presentation on how his work had been going the past couple of weeks. It was then time for the group question, and Keary had been wanting to go up and present my answers at least one time while I was there, and this was the last chance so I had to. The question was way beyond my knowledge however, but luckily I had Skyler there to help me out and I simply presented what was gonna happen in our answer and Skyler then actually presented how and why. Once the group meeting was over, Johny gave me a gift and a card everyone in the lab had signed and written a little personalized message on. Keary, Johny, Skyler, and I then went around the building to take pictures. I then said my final goodbyes and left the lab.

 

The following days I drove back to Ridgway, Colorado with my parents. We stopped by a few colleges on the way back as well as visited some families that live down in California. We took it super slowly the first few days while we were down in California, slowly moving east, and then finally came back on Tuesday through a ten hour drive. Overall, this experience has been super valuable, not only for the learning opportunity that it’s given me within the lab, but mostly the learning opportunities it’s given me outside the lab and living an almost college lifestyle. I’ll carry the experience and memories I’ve received on this internship throughout my life and am greatly thankful. Thank you, Sarah, and everyone at Pinhead who has made this possible.

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