Ibuprofen is the active ingredient in a number of over the counter pain relievers, e.g. Advil, Motrin, and Nuprin. It is one of the top-ten drugs sold worldwide, and, although it has been shown that only the S enantiomer has the desired biological activity, it is currently sold as the racemate. The synthesis begins with reaction of 4-isobutylacetophenone with the sulfur ylide produced by deprotonation of trimethylsulfonium iodide to yield an epoxide. (You should look this reaction up in an advanced organic text, e.g. the one by Jerry March.) The epoxide is then opened reductively by treatment with H2 and Pd catalyst to give an alcohol that is then oxidized to the acid, Ibuprofen, using KMnO4.
|Thursday II||Joy Manningfirstname.lastname@example.org|
|Thursday II||Kathleen Whiteemail@example.com|
The table below lists the chemicals that we will have available for this project. If you need something that is not on this list, consult with the mentor for your project. Also note the "Amount/group" column. This is the total amount of material available for each group to use on the project.
Cat. # 6284
|5 g||TA room|
|4 g||TA room||Irritant|
|Sodium Hydride (60% dispersion in mineral oil)||Aldrich
|5 g||TA room||Flammable Solid, Moisture Sensitive||Methyltriphenylphosphonium bromide||Aldrich
|10 g||TA room||Irritant, Hygroscopic|
|Butyllithium (1.6 M in Hexanes)||Aldrich
|20 mL||TA room||Flammable Liquid, Moisture Sensitive|
|DMSO (Dimethyl sulfoxide)||TA room||Wear gloves when handling DMSO. It is readily absorbed through the skin!|
|Pd, powder, submicron||Aldrich
|0.2 g||TA room|