Ethyl Diphenylphosphonoacetate [Horner-Emmons Reagent]

Typical Procedure: A solution of ethyl diphenylphosphonoacetate (0.50 mmol) in THF (10 mL) is treated with Triton B (0.27 mL, 0.60 mmol) at -78 ℃ for 15 min. Benzaldehyde (0.054 mL, 0.53 mmol) is then added, and the resulting mixture is stirred at -78 ℃. The reaction is quenched with saturated NH4Cl, and the mixture is extracted with AcOEt (10 mL×3). The combined extracts are washed with water (15 mL×2) followed by brine, dried (MgSO4) and concentrated. The isomers are separated by flash chromatography.