exp085_03-29-07.JPG

Objective

To analyze the reaction of crotonaldehyde with 5-methyfurfurylamine to see if imine can be obtained.

Procedure

Prepared solutions of Crotonaldehyde (83 uL, 1 mmol, 2 mL CDCl3, 0.5 M) and methylfurfurylamine (110 uL, 1 mmol, 2 mL CDCl3, 0.5 M). Mixed together in the presence of 3A molecular sieves. Allowed the imine reaction to continue over 3 days.

Results

Characterization of Starting Materials

Crotonaldehyde
Methylfurfurylamine (Used same methylfurfurylamine as used in Exp52)

Imine Formation

H NMR 1 hr 085A
H NMR 24.5 hrs 085B
H NMR 3 days 085C

Overlay

ImineRxn Overlay

Discussion

After 1hr, the reaction moves forward to the imine as the peak at 7.26ppm(imine peak) shows. Provided is a picture of the assigned peaks on the spectra after 1hr {characterization 1hr}.
After 24hours and more evidently after three days, side products emerge.
This may be cause by the furfuryl ring opening up as those two hydrogen peaks disappear. Further review needed.

Conclusion

This imine reaction was successful but with a lot of impurities.

Log

2007-03-29

16:50 Prepared solutions of crotonaldehyde(83 uL, 1 mmol, 2 mL CDCl3, 0.5 M) and methylfurfurylamine(110 uL, 1 mmol, 2 mL CDCl3, 0.5 M)
17:45 Mixed aldehyde and amine solutions together in a 13 mL vial in the presence of 65 (x mg) 3A molecular sieves..
17:50 Took 200 uL of imine solution and added about 2 mL of CDCl3 to take an initial H NMR
18:50 Took H NMR 1 hr. 085A

2007-03-30

17:58 Took sample of imine solution and without diluting used for HMR
18:22 Took H NMR 24.5 hrs 085B

2007-04-02

11:00 Took H NMR of imine solution 085C

Tags


crotonaldehyde InChI=1/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+
methylfurfurylamine InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3