Chemical Forums

Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: DahlEp on December 30, 2020, 05:53:30 PM

Title: Retrosynthetic analysis
Post by: DahlEp on December 30, 2020, 05:53:30 PM

I have difficulties understanding this topic...
I have to go from the top molecule, to all the reagents written on the first picture, by using retrosynthesis. I tried something but I'm sure I made a mistake with the diethyl malonate. Plus I don't understand where to use CH3-I and Cu-I. i thought about cross coupling reactions (I can only choose between Kumada/Suzuki/Heck/Goldberg/Ullman/Hartwig-Buchwald)
Could anyone please help me with this retrosynthesis and the forward reaction mechanism?
I'm really stuck  ???

Title: Re: Retrosynthetic analysis
Post by: rolnor on December 31, 2020, 06:25:41 AM

Can you make a 1,4-addition somehow, as a start?

Title: Re: Retrosynthetic analysis
Post by: DahlEp on December 31, 2020, 06:33:36 AM

Quote from: rolnor on December 31, 2020, 06:25:41 AM

Can you make a 1,4-addition somehow, as a start?

I tried. But I still can't figure out where I should use CH3-I and CuI. Someone I know said something about using CH3-I when going from diethyl malonate to ethyl methacrylate but I don't really understand it.

Title: Re: Retrosynthetic analysis
Post by: rolnor on December 31, 2020, 12:20:17 PM

You need CuI to catalyze the 1,4-addition of the Grignard. How can you then introduce a methyl group?