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Yield in a Horner Wadsworth Emmons reaction

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kriggy:

--- Quote from: Babcock_Hall on June 21, 2019, 11:23:48 AM ---I wonder if the deprotection conditions for FMOC cause self condensation of an aldehyde.  This would be useful to know in that I was contemplating working with the FMOC-version of the same compound later on.

--- End quote ---

You will very likely get de-fmocation which could easily account for low yield. The removal of fmoc with base like piperidine is super fast, the halflife of fmoc in presence of piperidine is like 10 seconds...
Loss of Fmoc group with molecular weight about 220 could easily account for the low yield, especially if you are using low. molecular weight aldehyde where the fmoc group is signigficant % of the mass of the compound.

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