[weyrich]

Hey all. I was given this molecule



and need to propose a synthesis and the only carbon sources are I can use are these



I don't know where to start and any help would be appreciated. Thanks!

Mod edit: IMG tages. Dan.

[kriggy]

you have to show some attepts (forum rule)

hint: try to cut the molecule into smaller ones which you know how to synthetise or you have in your carbon source list.

[weyrich]

I was thinking of turning the ethyl benzene into Acetophenone and then adding it to the pyrrole+benzene but I can't think of the reagents needed. I could somehow get the ethyl into a 2-ethylbenzeneol (probably not what its called, OH group in the middle of the attached ethyl) and then change that to the double bonded O with  H2CrO4 but again, not sure how to add the OH: perhaps H20 but not sure how to get it to bond specifically to that one spot on the ethyl.

Adding that group then to pyrrole+benzene i was thinking SnAr but whats to stop it from then adding to the C-2 or C-4 of benzene?

[kriggy]

You have the heterocycle you need in your list of reagents, no need to synthesise it

[weyrich]

Aye, Im not adding pyrrole to benzene I just don't know the name for it so I called it pyrrole+benzene

[weyrich]

So I have the ketone+SOCl2 to add a Cl to it. Then add benzene and AlCl3 to add the compound to benzene. Not sure if correct but i have no idea how to then add that to the pyrrolebenzene combo

[kriggy]

http://en.wikipedia.org/wiki/Indole

the 3 position of indole is highly nucleophilic and since the aldehyde group is deactivating they should react to form your product

[zsinger]

I like what Kriggy said.  That 3-indole position is highly activated.  If you know Suzuki Coupling, I see a 2 step synth, but that is somewhat advanced.  Hope this helps!
                 -Zack

Also-http://en.wikipedia.org/wiki/Leimgruber-Batcho_indole_synthesis