UCExp249-i.png

Objective

To synthesize a Ugi product from phenanthrene-9-carboxaldheyde, furfurylamine, phenylacetic acid and n-butylisocyanide on a larger scale in benzene. It had been proved in the previous experiment that this Ugi product does precipitate out from benzene. This experiment intends to measure an isolated yield for the compound.

Procedure

OUTLINE OF WHAT IS TO BE DONE
1.Dissolve phenanthrene-9-carboxaldehyde (62mg, 0.3mmol) in benzene (549uL) [total volume of the solution 549uL + 50.94uL = 600uL] 0.501M.
2. Add furfurylamine (27uL, 0.3mmol) to form an imine (not monitored). Vortex for 15s.
3. Make a 3M solution of phenylacetic acid in benzene by dissolving 409mg in 1mL solvent in a volumetric flask
4. Add phenylacetic acid (100uL of a 3M benzene solution) to the previously made imine solution. Vortex for 15s.
5. Add n-butyl isocyanide (31.2uL, 0.3mmol) to the reaction mixture. Vortex for 15s
Final concentration per component 0.395M
6. Obtain a picture of the solution.
7. Leave the vial undisturbed for 24h
8. Vortex for 15s, leave it undisturbed for 0.5h..if product precipitates obtain a picture...
9. Centrifuge, separate the supernatant. Wash the ppt with 0.5mL benzene (x3). Leave in a high vac desiccator for 5h. Weigh the product. Obtain HNMR, m.p and report yield.


Results

UCExp250-1A-i
UCExp250-1A-ii

Characterization of UC-250-2A

amount: 13 mg (6.5 % yield)
appearance:

HNMR

UCExp250-2A


Discussion

[Based on the known solubility of this Ugi product in benzene and the calculated rate of formation obtained from EXP249 is the isolated yield consistent with those measurements?]

Conclusion

Log

2009-10-06
21:30 Dissolved phenanthrene-9-carboxaldehyde (62mg, 0.3mmol) in benzene (549uL) in a 1dram vial. [total volume of the solution 549uL + 50.94uL = 600uL] 0.501M.
21:40 Added furfurylamine (27uL, 0.3mmol). Vortex for 15s.
21:45 Weighed out phenylacetic acid (409mg, 3mmol)
21:50 Placed the acid in a 1mL volumetric flask and added benzene; vortexed the solution to dissolve the solute, finally made-up the solution to 1mL mark by adding a few extra drops of the solvent.
22:00 Added the freshly prepared 3M solution of phenyl acetic acid (0.3mmol, 100uL) to the reaction mixture containing the aldehyde and amine solution. Vortexed the solution for 15s
22:05 Added n-butylisocyanide (31.2uL, 0.3mmol) to the reaction mixture. Vortexed for 15s.
22:15 Parafilmed the vial and obtained a picture of the solution; UCExp250-1A-i
2009-10-07
22:00 No solid observed yet..started sonicating
22:20 Removed from sonicator; no solid still
2009-10-08

10:20 Solid in the vial. Obtained a picture UCExp250-1A-ii
11:00 Vortexed the vial for 30s, centrifuged the contents and decanted the supernatant.
11:15 Added 0.5mL benzene to the reside, vortexed for 30s,centrifuged the contents and decanted the superntant in the previously accumulated supernatant. The process was repeated 3 times (3X wash)
12:00 After the washed a very small amount of residue was obtained which was set in high vac desiccator to dry.
2009-10-09
12:45 Obtained 13mg of a dry sample, now labeled UCExp250-2A
13:00 Obtained HNMR of UCExp250-2A
2009-10-15
11:00 Submitted UCExp250-2A for MS.