[ic2133]

Hello,
Can someone please help me synthesize the following molecule from it's precursor using specific reagents? I've included a picture of it.


I can't figure out if the oxygen of the ester in the product comes from the alcohol of the carboxylic acid or not. My guess was to make an ester out of the alcohol group by using SOCl/pyridine to replace it with a Cl group, then react with NaH/7-carbon halide to add that long alkyl chain (does that work?). So I end up with the left side of the product, but how do i remove the 2nd ketone (the right one) along with the carbons it's connected to?

If you can help, I would be so appreciative! It's the last problem i'm working on and it's driving me nuts!

Thank you!

[AC Prabakar]

Do you need only specific reagents to convert the reactant to product?or any alternate schems?

[Dan]

I can't figure out if the oxygen of the ester in the product comes from the alcohol of the carboxylic acid or not.

I suspect it probably does. Note that your starting material has a 7-carbon chain and so does your product...

Hint: my strategy would be to convert the starting material to heptanol, then acetylate it

[democanarchis]

You're overthinking this. You want to remove the carbonyl functionalities, then install the ester.