Exp085

== =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]