Objective

To verify if certain Ugi products can be precipitated out from a homogenous solution of the reactants in THF and DMSO at 1M final concentration of each component in the reaction mixture.

Results

solutions on day -1
solutions on day- 2
Spreadsheet


Discussion

Table i
Rxn Vial
No
Solvent
Ugi product
Aldehyde
Amine
Acid
Isocyanide
Conc per
component
3
THF
Ugi product 206B
benzaldehyde
furfurylamine
boc-gly
t-butyl isocyanide
1M
4
DMSO
Ugi product 206B
benzaldehyde
furfurylamine
boc-gly
t-butyl isocyanide
1M
5
THF
Ugi product 176
phenanthrene-9-carboxaldehyde
furfurylamine
boc-gly
n-butyl isocyanide
1M
The reactions listed above (Table i) formed a solid precipitate the next day, although the solids were not isolated and characterized, it is assumed that these are Ugi products. The reactions would have to be carried out again and the products would have to be characterized to confirm there structural identity.

Conclusion

Three reactions formed solid precipitates after one day. The reactions were carried out in THF at 1M concentration per component.

LOG

2009-04-03

15:50 Made-up a 2M solution of phenanthrene-9-carboxaldehyde in THF. This was done by dissolving phenanthrene-9-carboxaldehyde (412.5mg; 2mmol) in THF (1mL ) in a volumetric flask.
17:00 Five half dram vials were labeled1 through 5. Calculated amounts of solvents (see spreadsheet UCExp217) was added to each vial and capped tightly. [ Vial 4 used DMSO, remaining vials used THF]
17:20 To vial labeled 1, 2 and 5, a 2M solution of phenanthrene-9-carboxaldehyde solution in THF (100uL) was added. This was followed by the addition of amine; vial 1 &2 benzyl amine (0.2mmol, 21.8uL was added and to vial 5 - furfurylamine (0.2mmol, 17.6uL) was added. The solutions were vortexed for 30s each.
17:50 To vial 1- 4-chlorophenaylacetic acid (0.2mmol, 34.1mg), to vial -2 crotonic acid (0.2mmol, 17.2mg) and to vial -5 , boc glycine (0.2mmol, 35mg) was added. Each vial was vortexed for 30s after the addition.
18;30 n-butylisocyanide (0.2mmol, 20.9uL) was added to vials 1 and 5..the solutions were vortexed for 30s.
18:45 t-butylisocyanide (0.2, 22.6uL) was added to to vial 2. The solution was vortexed again for 30s.
19:00 To vials 3 and 4 aldready containing THF(109.3uL) and DMSO (109.3uL) benzaldehyde (0.2mmol, 20.3uL) and furfurylamine (0.2mmol, 17.6uL) was added and vortexed to 30s each.
19:20 Then boc glycine (0.2mmol, 35mg) was added to vials 3, and 4 and again vortexed for 30s each.
19:35 Lastly t-butylisocyanide (0.2mmol, 22.6uL) was added to vials 3 and 4...then each vials they were voxted for 30s each.
19:40 After all the additions to the vials, they were tightly screw capped and left undisturbed overnight for the product to form.
20:15 Obtained a picture of the vials containing the reaction mixtures.

2009-04-04

18:08 Obtained a picture of the solutions.[Next time wash and isolate for the ones where you have precipitates after 24 hours - 3 days is too long to wait JCB]