Previous Outburst

The previous outburst was generated by a frustrating aspect of my senior synthesis project. The full schematic is shown below:
The product (1) seems simple enough of a reaction to me. But, the cursed side product (dicyclohexylurea, DCU, a white solid) is driven strongly by Le Chatelier's principle. So, to slow it down, it's a good idea to stick it in a refrigerator once dicyclohexylcarbodiimide (DCC) had been added (if the reaction vessel wasn't iced, expect everything to crash out VERY quickly) [1].

So I thought I did everything well according to procedure. Prepare a round bottom flask with ~250mL THF, and dissolve the ether-acetic acid and hydroxysuccinimide in the vessel. Dissolve the DCC in ~50mL THF [2]. Ice both for ~30 minutes. Pour. Cap. Stick in refridgerator. Have beer.

So you would expect some DCU. But I didn't expect 13.8g, especially when I used ~14g of the DCC. Granted, I haven't done the calculations to determine how much of my DCC was lost to DCU, but ~13.8g seems like a bit much.

And I haven't even gotten all of it out of my reaction vessel. DCU is stubborn and wants to stay in my reaction vessel and not come out of solution. Plus, I think the pumps to the roto-vap lack sucking power and create a poor vacuum to remove the THF from the r.b.f.

At the end of the day I need a 140ppm solution of the pyrole-ether-acetate product. Hope for the best? If not, expect more inane bitching about synthesis. [3]

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[1] DCC is disgusting to use. It's a very chunky solid that requires chiseling to obtain. Secondly, it's very, very soluble in organic solvents and oils, particularly those found on your skin. So, it's readily absorbed through your skin. And, it's a sensitizer, so I feel bad for anyone who continuously uses DCC, like protein chemists. (Oh, and I know there's worse chemicals, but I'm not working with those at the moment)
[2] Oh, did I mention DCC has a high vapor pressure as a solid? Scared now? Muhahaha!
[3] Why oh why did i not change my concentration to chemical physics? The silly notion of being a well-rounded chemist has given me headaches, lol!