[filipe86portugal]

Hello everyone,

In the same molecule I have a triple bond and a carboxylic acid protected with a benzyl ester. I need to deprotect the benzyl ester but I want to keep the triple bond in the molecule and therefore I can´t use the conventional catalytic hydrogenation with Pd/C. I was thinking if I can use basic conditions to cleave the ester, but my question is if the triple bond is sensitive to basic conditions.

Thanks for your *delete me*

[TheUnassuming]

What reactions do you think your alkyne will be able to engage in with standard saponification conditions?

[Babcock_Hall]

There is some literature on deprotection of benzyl esters using iodotrimethylsilane or its equivalents (chlorotrimethylsilane plus sodium iodide).  I don't recall seeing anything about whether or not these conditions are compatible with an alkyne.