Trying to make some 3-triethylsilylpyridine to use as a standard for our reactions. Reaction seems straight forward enough.
![](https://sites.uni.edu/chin/wp-content/uploads/2019/04/image.png)
Get dry ice from local Hy-Vee (the one where Kurt Warner used to work). Cool stuff down. Looks like orange crush after the silane addition.
![](https://sites.uni.edu/chin/wp-content/uploads/2019/04/image-1-576x1024.png)
Crude NMR spectrum looked fairly messy.
![](https://sites.uni.edu/chin/wp-content/uploads/2019/04/image-2.png)
Tried a distillation to clean it up.
![](https://sites.uni.edu/chin/wp-content/uploads/2019/04/image-3-576x1024.png)
Not the best. Still a bunch of silanol.
Another distillation. A real on this time
![](https://sites.uni.edu/chin/wp-content/uploads/2019/04/image-4-1024x576.png)
NMR spectrum says cleanish, the GCMS says otherwise
![](https://sites.uni.edu/chin/wp-content/uploads/2019/04/image-5.png)
![](https://sites.uni.edu/chin/wp-content/uploads/2019/04/image-6.png)
Had to dig deep to clean this thing up. The old prep TLC. The best way to do chromatography. It is like the Hawaiian pizza of chromatography. The absolute best.
![](https://sites.uni.edu/chin/wp-content/uploads/2019/04/image-7-576x1024.png)
Only 66.6 mgs of product. But at least it was clean. And the final mass seems like a sign that I should not pursue this any further.