Exp246

= =

media type="custom" key="4296049"media type="custom" key="4296057" || media type="custom" key="4296031" ||
 * ===media type="custom" key="4296045"media type="custom" key="4296047" Benzene, r.t ->===

=Objective= To study the kinetics of a Ugi reaction in benzene =Procedure=

=Results= [|HNMR of 1,1,3,3-tetramethylbutylisocyanide] [|UCExp246 Spreadsheet] [|Integrations-1] [|SAMS for UCExp246]  **UCExp246-1A** **HNMR** [|Phenanthrene-9-carboxaldehyde in benzene] [|01min] [|02min] [|04min] [|08min] [|15min] [|16min] [|26min] [|28min] [|30min] [|32min] [|40min] [|50min] [|1h33min] [|1h42min] [|1h50min] [|2h00min]  [|2h08min]  [|2h48min] [|4h20min] [|5h50min] [|20h43min] [|28h00min]

[|22min] [|49min] [|1h28min] [|1h33min] [|1h43min] [|1h50min] [|3min] [|5min] [|7min] [|09min] [|22min] [|28min] [|34min] [|50min] [|58min] [|1h00min] [|1h16min] [|19h26min] [|61h43min]
 * UCExp246-2A**
 * UCExp246-3A **


 * [|246-4A HNMR]**

=Discussion= Calculations based on SAMS method indicate the concentration of phenanthrene-9-carboxaldehyde in the solution to be 0.66M insted of 0.6M. Change in the concentration of the aldehyde is observed despite an accurate measurement was performed while weighing and solution making. The micro-pipette used had been recently calibrated. Evaporation of the solvent (benzene) during the transfer in to the NMR tube may have resulted in an increase in the concentration of the aldehyde to 0.66M. Therefore this concentration was taken as the starting concentration of the aldehyde.

=Conclusion= =Log= 10:20 Obtained a NMR tube coaxial insert. 10:40 Made-up a 0.6M solution of phenanthrene-9-carboxaldehyde by dissolving 124mg (0.6mmol) in benzene in a 1mL volumetric flask. 11:00 Made-up a 3M solution of phenylacetic acid by dissolving 409mg (3mmol) in benzene in a 1mL volumetric flask. 15:00 Pipetted out 167uL (0.1mmol) of the 0.6M aldehyde solution in to the inner tube. Pipetted out 150uL DMSO-d6 in to the outer tube. Capped both the tubes immediately after placing the liquids in them. 15:09 Obtained HNMR of **phenanthrene-9-carboxaldehyde in benzene.** 15:10 Pipetted out furfurylamine (8.83uL) in to the inner tube containing the aldehyde. The reaction mixture will now be referred to as **UCExp246-1A** 15:11 Obtained HNMR of the the solution- UCExp246-1A-1min, only one transient and a relaxation delay of 50s -01min 15:12 Obtained HNMR of the the solution- UCExp246-1A-2min, only one transient and a relaxation delay of 50s - 02min 15:14 Obtained HNMR of the the solution- UCExp246-1A-4min, only one transient and a relaxation delay of 50s - 04min 15:18 Obtained HNMR of the the solution- UCExp246-1A-8min, only one transient and a relaxation delay of 50s - 08min 15:25 Obtained HNMR of the the solution- UCExp246-1A-15min, four transient and a relaxation delay of 50s - 15min 15:26 Obtained HNMR of the the solution- UCExp246-1A-16min, only one transient and a relaxation delay of 50s - 16min 15:36 Obtained HNMR of the the solution- UCExp246-1A-26min, four transient and a relaxation delay of 50s - 26min 15:38 Obtained HNMR of the the solution- UCExp246-1A-28min, only one transient and a relaxation delay of 50s - 28min 15:40 Obtained HNMR of the the solution- UCExp246-1A-30min, only one transient and a relaxation delay of 50s - 30min 15:42 Obtained HNMR of the the solution- UCExp246-1A-32min, only one transient and a relaxation delay of 50s - 32min 15:50 Obtained HNMR of the the solution- UCExp246-1A-40min, four transient and a relaxation delay of 50s - 40min 16:00 Obtained HNMR of the the solution- UCExp246-1A-50min, four transient and a relaxation delay of 50s - 50min 16:43 Obtained HNMR of the the solution- UCExp246-1A-1h33min, four transient and a relaxation delay of 50s - 1h33min 16:52 Obtained HNMR of the the solution- UCExp246-1A-1h42min, four transient and a relaxation delay of 50s - 1h42min 17:10 Obtained HNMR of the the solution- UCExp246-1A-2h, four transient and a relaxation delay of 50s - 2h 17:18 Obtained HNMR of the the solution- UCExp246-1A-2h08min, four transient and a relaxation delay of 50s- 2h08min 17:58 Obtained HNMR of the the solution- UCExp246-1A-2h48n, four transient and a relaxation delay of 50s - 2h48min 19:30 Obtained HNMR of the the solution- UCExp246-1A-4h20min, four transient and a relaxation delay of 50s - 4h20min 21:00 Obtained HNMR of the solution - UCExp246-1A-5h50min, four transients and a relaxation delay of 50s - 5h50min 11:53 Obtained HNMR of the solution - UCExp246-1A-20h43min, four transients and a relaxation delay of 50s - 20h43min 19:10 Obtained HNMR of the solution - UCExp246-1A-28h, four transients and a relaxation delay of 50s - 28h 19:15 Pipetted out phenylacetic acid (33.4ul, 3M in benzene) in to the inner tube of the NMR set of tubes containing the reaction mixture. The solution in the tube will now be referred to as **UCExp246-2A** 19:16 Placed the tube in the instrument..unable to achieve lock or obtain a decent sepctrum..shimmed over again 19:38 Obtained an HNMR, UCExp246-2A-22min 20:05 Obtained an HNMR, UCExp246-2A-49min 20:43 Obtained an HNMR, UCExp246-2A-1h28min 20:48 Obtained an HNMR, UCExp246-2A-1h33min 20:58 Obtained an HNMR, UCExp246-2A-1h43min. 21:05 Obtained an HNMR, UCExp246-2A-1h50min 21:12 Pipetted out 1,1,3,3-tetramethylbutylisocyanide (17.5uL, 0.1mmol). The reaction mixture will now be referred to as **UCExp246-3A** 21:15 Obtained an HNMR of UCExp246-3A-3min 21:17 Obtained an HNMR of UCExp246-3A-5min 21:19 Obtained an HNMR of UCExp246-3A-7min 21:20 Obtained an HNMR of UCExp246-3A-9min 21:34 Obtained an HNMR of UCExp246-3A-22min 21:40 Obtained an HNMR of UCExp246-3A-28min 22:02 Obtained an HNMR of UCExp246-3A-50min 22:10 Obtained an HNMR of UCExp246-3A-58min 22:28 Obtained an HNMR of UCExp246-3A-1h16min 16:38 Obtained an HNMR of UCExp246-3A-19h26min 10:43 Obtained an HNMR of UCExp246-3A-61h43min 12:02 Obtained an HNMR of UCExp246-3A-86h50min 12:22 Obtained an HNMR of UCExp246-3A-87h10min 07:34 Obtained an HNMR of UCExp246-3A-106h22min 08:08 Obtained an HNMR of UCExp246-3A-118h56min 11:00 Poured the contents of the sealed NMR tube in to a one dram vial, added ~2mL benzene to it. 11:10 Added 1mL 1M HCl (aq) to the vial, vortexed it for 15s and let it separate out. 11:20 Removed the bottom aqueous layer carefully using a glass pipette. Then added another 1mL 1M HCl (aq.) and vortexed the vial again for about 15s, after the layer separated out, the bottom aqueous layer was once again removed with the pipette. 11:40 Now added 1mL of 10% NaOH (aq), vortexed the solution again for approximately 15s, and then removed the bottom aq. layer with a pipette. Repeated the wash with another 1mL 10% NaOH (aq). 11:55 Pipetted in to the vial 1mL saturated brine solution, vortexed, left the vial to settle down and separated the layers. 12:05 Added about 1g of anydrous MgSO4 to the vial. Vortexed it again, centrifuged and decanted the clear supernatant. 12:15 Washed MgSO4 in the vial with benzene (1mL), centrifuged and decanted the supernatant in the previously collected supernatant. 12:30 The combined supernatant were then set under a gentle flow of N2 to remove solvent (benzene). This was done to concentrate the product...by evaporating extra solvent.. 14:00 Obtained an yellow oily liquid, this liquid is now labeled **246-4A** 14:10 Dissolved246-4A in DMSO-d6 and obtained an HNMR
 * 2009-08-20**
 * 2009-08-21**
 * 2009-08-22**
 * 2009-08-24**
 * 2009-08-25**
 * 2009-08-26**
 * 2009-08-27**
 * 2009-08-31**