[1] Controllable Phosphorylation of Thioesters: Selective Synthesis of Aryl and Benzyl Phosphoryl Compounds. J. Org. Chem. 2020, 85, 22, 14653–14663.
A dried 250 mL flask was charge with butylmagnesium chloride (20.0 mmol, 2 mol/L in THF) in an ice-water bath under N2. A solution of ethyl phenylphosphinate (10.0 mmol) in anhydrous THF (5 mL) was then added dropwise over 30 min. Then, the mixture was further stirred at ambient temperature overnight and then cooled to 0 °C again. HCl (100 mL, 0.1 N) was then added dropwise. The mixture was extracted with dichloromethane (100 mL × 3), and the combined organic phase was washed with saturated NaCl solution, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. The crude product was purified by column chromatography (EtOAc) to give the desired product Phosphine oxide, butylphenyl-.
