This is what I'm asked to explain:
![](https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FlKiHxlE.png&hash=8c272468def8ef7cd1eca18f369ae8fb74e7a407)
As you can see, they give me 4 starting reagents and 1 final product, I'm supposed to explain that synthesis.
This is my attempt:
![](https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FYNE5hTN.jpg&hash=5c2340257c622120371e8d205f2c1ef148da94dd)
I think my route and mechanisms are OK, (please, check them), but as you can see, I don't even use one of those 4 starting compounds (the one that is an ester), and I introduce the extra carbon I need as Methyllithium.
Since this is going to be a graded exercise, I really need to know if there is another wayof obtaning the product using all the starting reagents. I don't see that way, specially when the sum of the carbons of those 4 reagents (without counting OEt, which would act as leaving group) is one more than there are in the final product (maybe lose of CO2? where?? and how???)
I also attempted using the ester:
![](https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FmC98ppU.jpg&hash=f58f0a574290b9b8a42f4225cac439590eaba99d)
But as you can see, in this case I don't see how can I add the Phenyl to the compound using the benzoic acid (which is one C more than I need). If it where bromobenzene, or benzene, I could simply add it as a grignard to the aldehyde -30ºC to obtain ketone... But is not the case.
I don't see other way more than the one I posted first, but I feel that's kinda "cheating", since I don't use one of the reagents and I use MeLi in exchange.
Any thoughts?