Marshall Moritz


To synthesize a Ugi adduct from phenanthrene-9-carboxaldehydeand phenyl acetic acid with different amines and isocyanides in benzene



UCExp242 Vials 1-5
UCExp242 Vials 6-10
UCExp242 Precipitate 20h

Spreadsheet UCExp242



9:24--Six scoops of phenanthrene-9-carboxaldehyde were added to a one-dram vial labelled "vial 1", of benzene.
9:26--Vial 1 was vortexed for ten seconds and sonicated for 30 minutes. The water in the sonicator was recorded to be 22.0C at the beginning of sonication and 32.5 at the end of sonication.
10:04--VIal 1 was removed from the sonicator and sat out to cool to room temperature
10:24--As the temperature of the lab was quite high, 29.0C, vial 1 was put in a water bath of 23.0C for 30 minutes to cool it to normal room temperature.
11:30--NMR of vial 1 was taken on the 500MHz machine to find the solubility of phenanthrene-9-carboxaldehyde in benzene at room temperature.

11:24--Added 1.2284g of phenylacetic acid to 3mL of benzene to make a 3M solution.
11:30--Added 0.3727g of phenanthrene-9-carboxaldehyde to 3mL of benzene to make a 0.6M solution.
12:02--Labelled 10 vials 239-1 through 239-10
12:14--Added 0.1mmol, 33.3uL of phenylacetic acid in benzene into each vial
12:43--Added 0.1mmol, 166.66uL of phenanthrene-9-carboxaldehyde in benzene into each vial
13:18--Pipetted 0.1mmol, 8.8uL of furfurylamine into vials 1-5
13:31--Pipetted 0.1mmol, 11.1uL of methylfurfurylamine into vials 6-10
13:44--Pipetted 0.1mmol of isocyanide (see spreadsheet for volumes and isocyanide) into each vial
13:57--Vortexed each vial for 15 seconds
14:01--Obtained a picture of all 10 vials after addition of all reactants

9:50--Precipitate formed in vials 4 and 5 after 20 hours. A picture was obtained of vials 3, 4, and 5 to show the precipitate in contrast to samples without precipitate.
11:25--Washed vials 4 and 5 with 150uL of benzene
11:27--Capped vials and vortexted for 30 seconds.
11:28--Centrifuged vials 4 and 5 for 2 minutes
11:30--Decanted vials 4 and 5, saving the mother liquors in separate, labelled vials
11:32--Vortexted vials 4 and 5 for 15 seconds each to break up the solid on the bottom of the vial
11:34--Repeated washing procedure two more times to completely purify the Ugi product. On the third time, the rubber lining of the cap of vial 4 fell into the vial filled with benzene. The lid was quickly removed from the vial with a needle.
12:13--Placed vials 4 and 5 in the desiccator for sevreal hours until the product was dry.