[Elan]

I've been trying to convert a ketone to an alkene using Tebbe's reagent. Trouble is, there is a distant ester on the molecule that keeps getting converted as well. I've tried playing with the temperature many times over, but I just can't seem to get one reaction to happen without the other. Have any of you ever had a similar issue?

[Archer]

I've been trying to convert a ketone to an alkene using Tebbe's reagent. Trouble is, there is a distant ester on the molecule that keeps getting converted as well. I've tried playing with the temperature many times over, but I just can't seem to get one reaction to happen without the other. Have any of you ever had a similar issue?

Unfortunately It's known for reacting with esters as well as ketones, have you considered protecting the ester as an orthoester?

[Elan]

Unfortunately It's known for reacting with esters as well as ketones, have you considered protecting the ester as an orthoester?

That's a good idea, but it's an extra step that I'd like to avoid if I can...

[Archer]

Wittig reaction then? I am not sure how selective this is though.

 I don't recall the Wittig reaction converting esters.

[discodermolide]

I have had several of my esters undergo a Wittig! Methyl and ethyl.

[Archer]

I have had several of my esters undergo a Wittig! Methyl and ethyl.

Oh, clearly I have never run these with esters present.

[discodermolide]

Here is some literature for the Wittig with esters.
A. P. Uijtterwaal, F. L. Jonkers, A. van der Gen, J. Org. Chem., 1979, 44(18), 3157.
A. P. Uijtterwaal, F. L. Jonkers, A. van der Gen, J. Org. Chem., 1978, 43(17), 3306.
W. W. Epstein, L. A. Gaudioso, J. Org. Chem., 1982, 47, 175.