Researcher

Marshall Moritz

Objective

To synthesize a Ugi adduct from phenanthrene-9-carboxaldehyde, furfurylamine, and phenyl acetic acid with different isocyanides in benzene

Procedure


Results

Pictures
UCExp244 Vials 4-5
UCExp244 1h
UCExp244 Precipitate 24h
UCExp244 Solids
Mass Spec
UCExp244-4A Nominal Mass
UCExp244-4A HRMS
UCExp244-5A Nominal Mass
UC244-5A HRMS
Yield Vial 4: 8.9724-8.8066 = 0.1658g
Yield Vial 5: 8.9638-8.7900 = 0.1738g

HNMR Vial 4
C13NMR Vial 4

HNMR Vial 4A

Discussion

From the HNMR and 13CNMR, it is clear that a proper Ugi product was not formed in this reaction. There are missing peaks for the isocyanide, which should appear between 0.5 and 2.0ppm, and for the phenanthrene which appears in the aromatic region, around 7.5ppm. The peaks for furan and phenylacetic acid are very present in the spectra, and the data from the 13CNMR suggests that only 9 or 10 carbon atoms are present in the product. Thus the proposed structure for the product of the reaction was an ammonium salt; phenylacetic acid and furan both attached to a central nitrogen atom. [No phenylacetic acid is not directly attached to the nitrogen - this is just furfurylammonium phenylacetate - put up a pic for clarity JCB]
UCExp244-4A_5A-salt.jpg

Log

2009-08-03
10:44--Added 0.6170g of phenanthrene-9-carboxaldehyde to 5mL of benzene to make a 0.6M solution.
11:01--Labelled 2 vials 244-4 and 244-2
11:34--Added 1.0 mmol, 333.3uL of phenylacetic acid in benzene into each vial from stock solution
11:46--Added 1.0 mmol, 1666.6uL of phenanthrene-9-carboxaldehyde in benzene into each vial from stock solution
11:57--Pipetted 1.0 mmol, 88uL of furfurylamine into each vial
12:01--Pipetted 1.0 mmol of isocyanide (see spreadsheet for volumes and isocyanide) into each vial
12:07--Vortexed each vial for 30 seconds
12:09--Obtained a picture of all vials after addition of all reactants
12:29--Solid had formed in both vials after 20 minutes
1:30--Obtained a picture of both vials after 1 hour

2009-08-04
9:23--Precipitate formed in vials 4 and 5 after 24 hours. A picture was obtained of vials 4 and 5
9:26--Washed vials 4 and 5 with 150uL of benzene
9:27--Capped vials and vortexted for 30 seconds.
9:28--Vacuum filtered vial 4 with a Buchner funnel. Emptied vial 4 onto vacuum filter, washed out vial with 100uL of benzene two times. Washed product on filter with 150uL of benzene two times. Left on vacuum for 13 minutes.
9:44--Removed contents of vial 4 from vacuum to sit and dry
9:47--Repeated vacuum filtration process described above for contents of vial 5.
10:04--Weighed 2 empty vials labelled 4a and 5a and recorded mass.
10:07--Added dried products 4 and 5 to their respective vials and reweighed to find the yield of each product.
11:20--Took an HMNR and C13NMR of vials 4 and 5 on the 300MHz Varian instrument