Wittig-Horner reaction Triethyl phosphonoacetate

Data Characterizing the Wittig—Horner Reaction between Furfural and Triethyl Phosphonoacetate in the Presence of Basic Catalysts in a Batch Reactor (294)... 

Wittig-Horner reaction a,p-unsaturated esters. The reaction of triethyl phosphonoacetate (1) with aldehydes can be carried out in water using potassium carbonate at 20° or potassium hydrogen carbonate at 100°. 

The Wittig-Horner (W-H) reaction is a versatile method for the synthesis of functionalized alkenes. The synthesis of 3-substituted ethyl acrylates and acrylonitriles, which are used as monomers in polymerization, were successfully carried out by the reaction of triethyl phosphonoacetate or cyanomethanephosphonate, respectively, with various aldehydes with activated Ba(OH)2 as the catalyst in the presence of dioxane solvent at 343 K (294). As was observed for other basic solid... 

The protected methyl glycoside 3 is converted to the corresponding aldehyde by Swern oxidation using oxalyl chloride activated DMSO. Further reaction with triethyl phosphonoacetate and sodium hydride -known as the Horner-Wadsworth-Emmons reaction - provides selectively the trans et /Tun saturated ester 4 in 72 % yield. This valuable alternative to the Wittig olefination protocol uses phosphonate esters as substrates which are readily available from alkyl halides and trialkyl phosphites via the Arbuzov rearrangement.9 co2Et Reaction of the phosphonate with a suitable base gives the... 

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