Objective

To synthesize three Ugi products using 4-pyrenebutanoic acid in a bisolvent system- methanol and THF.

Procedure


Results


UCExp219-1
UCExp219-2
UCExp219-3
Spreadsheet

Discussion

After adding all components to vial 219-A, a homogeneous solution could not be obtained..therefore this reaction has to be rerun either at a lower final concentration of each component in the same solvent system or the reaction has to be run in THF at 1M final concentration of each component.
However reaction vials 219-2 and 219-3 formed solid after three days. Therefore in order to have a practical synthesis, where a solid product could be obtained with in one day, for these two reaction, again THF may be desirable as a solvent and the reactions could be run at a higher final concentration per component, possibly 1.5M

Log

2009-04-17

20:30 Three one dram vials were labeled 219-1A, 219-2A and 219-3A. To vial 219-1A THF (58uL) , 219-2A THF (26uL) and to vial 219-3A THF (47uL) was added. The volume of THF to added to each vial was calculated assuming volumes of each component to be added to each vial were additive. Volumes for solid reactants was calculated using predicted densities from Chemspider.
21:00 To vial labeled 219-1A, methylamine (2.0M methanolic solution, 1mL, 2mmol) was added using a syringe. This was followed by the addition of 2-naphthaldehyde (2mmol, 312.4mg) and a quick vortex for 30s. Subsequently 4-pyrenebutanoic acid (2mmol, 576.7mg) was added and then the vial was vortexed for 30s..the solid did not dissolve. Not withstanding this t-butylisocyanide (2mmol, 226.2uL) was added to it. The solution was vortexed for 30s.
21:15 To vial 219-2A containing THF, methylamine (2.0M methanolic solution, 500uL, 1mmol) was added using a syringe. This was followed by the addition of 4-(N,N-dimethyl)aminobenzaldehyde (1mmol, 149.2mg) anda quick vortex for 30s. Subsequently 4-pyrenebutanoic acid (1mmol, 288.3mg) was added and then the vial was vortexed for 30s..the solid dissolved completely in the solution. Then t-butylisocyanide (1mmol, 113.1uL) was added to it. The solution was vortexed for 30s.
21:35 To vial 219-3A containing THF, methylamine (2.0M methanolic solution, 500uL, 1mmol) was added using a syringe. This was followed by the addition of 4-methylbenzaldehyde (1mmol, 117.9uL) and a quick vortex for 30s. Subsequently 4-pyrenebutanoic acid (1mmol, 288.3mg) was added and then the vial was vortexed for 30s..the solid did not dissolve. Not withstanding this t-butylisocyanide (1mmol, 113.1uL) was added to it. The solution was vortexed for 30s.
21:44 Obtained a picture of the vials - UCExp219-1.
21:45 The vials were left undisturbed over night.

2009-04-18

11:00 The solution in vial 219-3A had become homogenous- clear.
11:20 The solutions in the vials were vortexed for 30s each.
11:40 Entire reaction mixture in vial 219-1A has turned solid.
11:45 Obtained a picture of the vials. UCExp219-2

2009-04-20

14:28 Crystals have appeared in the vials 219-2A and 219-3A. Obtained a picture of the vials; UCExp219-3