compound1

Lydia Owusu & Gloria Tucker 1. Isopropyl grinard. 2. grinard with 2-methyl propanal reacts with H+ to make OH 3.oxidize OH to a ketone 4.ketone with a Wittig Reaction (**triphenyl phosphonium ylide)** This looks good. The magnesium you start with is elemental metal, not the oxidized form. Other than this, it looks great. Bruce Bondurant Type in the content of your page here.

Actual work on how to synthesize this to come. I was just using the 3D model builder in Chem Sketch and I wanted to try to add a picture to the Wiki. Jason DeMao 4/15/

Nice, I hadn't tried this before Bruce Bondurant

We thought about what you said and wanted to try this route. Gloria Tucker, Lydia Owusu. A grigard is a good idea, but you need to keep track of your carbons. the reaction of the grignard of 2-methyl-1-bromo propane with propanal will give you 5-methyl-3-hexanol, not the branched compound that you are looking for. If you were to react isopropyl grignard with 2-methyl propanal, then you would get the compound that you want. In the last step, There is no way that treatment of 2,4-dimethyl-3-pentanol will give you the alkene that you show here. Instead it will give you the elimination product, 2,4-dimethyl-2-pentene. I dont know of any reaction that will directly form a carbon-carbon bond to an alcohol like this. You would have to either turn the alcohol into a halide, then a grignard, and react with an electrophile like formaldehyde followed by elimination, or you would have to oxidize to ketone and treat it with methyl-triphenylphosphine yilid. The later would probably give you the best results. Try using models to follow the reaction. It is sometimes easy to get lost int the trees when you just use pencil and paper. Bruce Bondurant

per Jason DeMao

Jason DeMao



Jason: I think that the use of the isopropyl grignard to form the alcohol is a good start. Once you form the 3-bromo-2,4-dimethyl pentane, how do you put on the double bond to the methylene. Could you use a grignard to make an alcohol? Remember that if you can make the primary amine, you could get a cope or hofmann elimination to form the les substituted alkene. Could you also convert to a ketone instead of a bromide? If so, how could you form the double bond from there? Bruce Bonduant