Reagent for Z-Preferential HWE Reaction to Introduce (Z)-α,β-Unsaturated Esters
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Ethyl Di-o-tolylphosphonoacetate [D2548] is a reagent for the Z-preferential Horner-Wadsworth-Emmons (HWE) reaction, known as the Ando method, and it can be used to easily introduce (Z)-α,β-unsaturated esters. As an example, ethyl di-o-tolylphosphonoacetate (1.5 eq.) was deprotonated with Sodium Hydride (60%, dispersion in Paraffin Liquid) [S0481] in dry THF at −78 °C, then reacted with p-Tolualdehyde [T1073] at the same temperature for 2 hours. After aqueous workup and purification by silica gel column chromatography (toluene:diethyl ether = 40:1), the product was obtained as a colorless oil in 91% yield with an E:Z ratio of 1:1.29. The reaction was monitored by UPLC, and the E:Z ratio was estimated from ¹H-NMR.
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Source
- TCI Practical Example: www.tcichemicals.com/ID/en/product/tci-topics/TCIPracticalExample_20251201
- TCI product page T1073: tcichemicals.com/ID/en/p/T1073
For research and laboratory use only, not for human consumption.
