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UC on ChemSpider
Alicia's Masters Thesis
Open Web Drug Dev.
To Do List
Ugi NMR Analysis
To check the stability of the furan ring of 5-Methylfurfurylamine in TFA to investigate
the behavior of furan containing Ugi products
In an NMR tube 5-methyl furfurylamine (20uL, 0.179mmol, 0.179M) is dissolved in CDCl3 (500uL). An initial HNMR of the solution is obtained on a 300MHz NMR instrument. To the solution in the NMR tube, Trifluroaceticacid (500uL, 50%) is added and the reaction is monitored by NMR.
After 6 days
HOMODEC of 73A
The methylene group is apparently the quartet at 4.3 ppm with a coupling of 6 Hz. The fact that it is coupling to NH3+ is confirmed by a selective homonuclear decoupling experiment ( HOMODEC of 73A ). This was done by irradiating the NH3+ peak at 7.05 ppm, as a result of which the CH2 quratet collapsed to a singlet
After 6 days it is clear that there is nothing happening to the furan ring. The 5-methylfurfurylammonium trifluroracetate is stable and does not lose its furan character or the methyl group in 1:1 TFA/CDCl3.
12:30 Made-up a solution of 5-methyl furfurylamine (20uL) in CDCl3 (500uL)
12:45 Obtained HNMR of 5-MFA
13:20 Added TFA (500uL) to the above solution, obtrained (
14:00 Obtained HNMR (t = 40min)
16:08 Obtained HNMR (t = 2h 48min)
12:41 Obtained HNMR of 73A (t = 6 days)
21:00 Obtained HOMODEC of 73A. The compound remained unchanged.
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