[Dan]

I have a benzyl ester functionality which is in very close proximity to a benzyl ester.

Benzyl esters are not very hindered, organilithium reagents react with esters. Maybe this is the problem.

[orgopete]

I have a benzyl ester functionality which is in very close proximity to a benzyl ester.

Benzyl esters are not very hindered, organilithium reagents react with esters. Maybe this is the problem.

I agree. Just try the metal-halogen exchange and quench the reaction with water or D2O. Do you recover the hydrido compound?

[Nescafe]

You guys were right. Mobius`s conditions works, did a test reaction with a simpler starting material, just not with my stuff.

For some reason I thought the benzyl ester was not a problem, but it was indeed. Fledramus was spot on.

Thanks,

Nescafe.

[Mobius1988]

Glad to hear you figured it out.

Just a tip for the future if you ever use this reaction again...you cant do it using my method if you have the potential for SNAr reactions to occur because the dimethylamine will readily attack there (as i unfortuntely found out). But found a paper where they do the same reaction but do an aqueous/organic work up in between to get the aldehyde and then reduce that separately.