Taber's reagent

An addition of trimethyl phosphite to 1 yielded phosphonate 2, which can be purified by distillation to obtain the desired reagent (3).

It is very similar, both structurally and in its usage, to the Ohira-Bestmann reagent which is used for the same chemical process of aldehyde to alkyne homologation.

This modification is possible since the acyl group is lost before the diazo phosphonate (Taber's reagent in this case) reacts with the aldehyde.

This is pertinent since fast reactions (click chemistry) has become more popular, making a reaction of this type for creating terminal alkynes necessary[1] The Taber reagent works on primary, secondary, and tertiary aldehydes.

Examples of aldehyde to terminal alkyne homologations using the taber reagent are shown.

Scheme 1.
The experimental work of Taber et al., showing the efficacy of Taber's reagent in changing primary, secondary, and tertiary aldehydes into alkynes. [ 1 ]