ETHYL 2-[BIS(2,2,2-TRIFLUOROETHYL)PHOSPHONO] PROPIONATE

Chemical Properties

Colourless Liquid

Uses

A wittig reagent.

Synthesis

KHMDS (7.50 mL, 3.75 mmol, 0.5 M in toluene) was added to a solution of 18- crown-6 (4.10 g, 15.51 mmol), THF (20 mL), and bis (2,2,2-trifluoroethyl) phosphite (1) (0.50 mL, 3.41 mmol) by syringe in a dropwise manner at -78 ℃. Following 15 min, ethyl 2-bromopropionate (0.40 mL, 3.08 mmol) was added to the round bottom flask and the reaction mixture was allowed to stir for 4 hr at room temperature. Following the standard workup procedure, the crude product was then purified by flash column chromatography (3:1 to 2:1 hexanes:EtOAc, Rf = 0.33 in 1:1 hexanes:EtOAc) yielding Ethyl 2-[Bis(2,2,2-trifluoroethyl)phosphono] Propionate (112 mg, 0.33 mmol, 10.5%) as a yellow syrup.