Objective

To synthesize eight Ugi products with piperonal, furufylamine and 1-pyrenebutyric acid with eight different isocyanides in THF.

Procedure

A homogeneous solution of piperonal (5mmol, 750.6mg), furfurylamine (5mmol, 441.8uL) and 1-pyrenebutyric acid (5mmol, 1441.7mg) was made up in a 10mL volumetric flask. The solution (500uL, 0.25mmol per component) was transferred in to eight labeld one dram vials. To each vial a unique isocyanide (0.5mmol) was added. The obtained solutions were vortexed for 10s each to ensure a homogeneous solution was obtained. The vials containing the reaction mixtures were left undisturbed overnight at room temperature.

Results

Spreadsheet
IMG-UCExp227-O
IMG-UCExp227-1

Discussion

Accidentally twice as much isocyanide (0.5mol) was added to each vial than any of the other components (500uL of 0.5M solution, 0.25mmol).

Conclusion

No Ugi products precipitated out. NOTE - Excess isocyanide was used.

Log

2009-05-22
18:00 Dissolved piperonal (5mmol, 750.6mg) in about 1mL THF in a 5mL volumetric flask, then added furfurylamine (5mmol, 441.8uL) to it. Vortexed the solution for 30s to obtained a homogeneous solution.
18:30 Weighed out 1-pyrenebutyric acid (5mmol, 1.4417g), transfered it carefully in to the 5mL volumetric flask. Added THF up to the mark..vortexed for 30s, unable to dissolve the acid in the the solution.
19:10 Parafilmed the volumetric flask and placed it in a sonicator with water bath at room temp (24C).
19:30 Removed from the sonicator, the solid did not dissolve.
19:35 Transferred the solution from the 5mL volumetric flask in to a 10mL volumetric flask, rinsed out the 5mL flask with small (500uL) portions of THF and added it to 10mL flask...
19:45 Added extra THF to the 10mL volumetric flask and made it up to the mark...the solid went in the solution easily, therefore vortexed it for only 10s.
19:55 Obtained a picture of the 10mL volumetric flask containing 5mmol of the piperonal, furfurylamine and 1-pyrenebutyric acid..The concentration per component in this solution of THF is 0.5M...1mL of this solution dispenses 0.5mmol of each component. This solution is labeled 227-O.
20:00 Obtained a picture 227-O
20:10 Labeled eight vials as 227-1, 227-2, 227-3, 227-4, 227-5, 227-6, 227-7 and 227-8.
Placed 500uL of the solution 227-O in to the above labeled eight vials
20:20 Added the following isocyanides to the corresponding vials. After the addition of the isocyanide to the vials they were vortexed for 10s and made sure a homogeneous solution was obtained.
Sample Number
Isocyanide added
Amt of
isocyanide added(0.5mmol)
227-1
t-butylisocyanide
56.5uL
227-2
n-butylisocyanide
52.3uL
227-3
n-pentylisocyanide
63uL
227-4
cyclohexylisocyanide
62.2uL
227-5
benzylisocyanide
61uL
227-6
TOSMIC
97.6mg
227-7
Morpholinoethyl isocyanide
69uL
227-8
2-chloro-6-methylphenyl isocyanide
75.8mg
20: 45 Obtained a picture (IMG-UCExp227-1) of the vials containing eight solutions. All solutions formed a clear homogeneous solutions. Vials were left at room temp (24C) for a 24h wait.
2009-05-23
19:00 No solid precipitated in any vial.