To synthesize three Ugi products using phenanthrene-9-carboxaldehyde in THF.




Although two of the three reaction attempted [221-1(148C) 221-2 (150D)] in this experiment had formed solid Ugi products in methanol previously, none of the reactions in this experiment formed a solid ppt. The reactions were carried out in THF.


No solid Ugi product was obtained from the reactions performed in THF.



16:00 Dissolved phenanthrene-9-carboxaldehyde (412.4, 2mmol) in THF and made it up to the mark in a 1mL volumetric flask. The solution needed to be sonicated for 20min between 21-23C inorder to make a homogeneous solution. This is a 2.0M solution.
16:20 Prepared a 6M crotonic acid solution in THF by dissolving 6mmols (516.5mg) in 1mL THF in a 1mL volumetric flask.
22:00 Labeled three vials 221-1, 221-2 and 221-3.
22:10 Pipetted-out 200uL (0.4mmol) of the previously prepared 2M phenanthrene-9-carboxaldehyde solution to each vial.
22:15 Transferred heptylamine (0.4mmol; 59.3uL) to vial labeled 221-1; benzyl amine (0.4mmol, 43.7uL) to vial 221-2 and 5-methylfurfurylamine (0.4mmol, 44.6uL) to vial labeled 221-3. Vortexed the vials for 10s each.
22:25 Then to each vial added 67uL of the previously prepared 6M crotonic acid solution in THF(0.4mmol). The vials were then vortexed for 10s each.
22:30 Pipetted-out t-butylisocyanide (45.2uL, 4mmol) in to each vial. Vortexed each vial for 10s each.
22:35 Finally added 28.5uL THF to vial 221-1, 44.1uL THF to vial 221-2 and 43.2uL THF to vial 221-3. Vortexed the vials again for 10s.


20:00 Obtained a picture of the solutions.