Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester

Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester 화학적 특성, 용도, 생산

• 용도

  Methyl 2-[Bis(2,2,2-trifluoroethoxy)phosphinyl]propionate is synthetic reagent used in Z-selective HWE reactions (a.k.a. Still-Genari modification) to make alpha,β-unsaturated esters. Methyl 2-[Bis(2,2,2-trifluoroethoxy)phosphinyl]propionate is used as reagent/reactant for preparation of (±)-(Z)-2β-hydroxy-14-hydro-β-santalol via tandem radical cyclization.

• Synthesis

  KHMDS (8.0 mL, 4.00 mmol, 0.5M in toluene) was added by syringe to a solution of dried 18-crown-6 (4.20 g, 15.89 mmol), THF (20 mL), and Bis (2,2,2-trifluoroethyl) phosphite  (0.55 mL, 3.75 mmol) at -78 ℃. Following 15 min, methyl 2-bromopropionate (0.35 mL, 3.14 mmol) was added to the reaction flask. The reaction mixture was allowed to warm to room temperature for 4hr. The standard workup protocol was followed, then the crude product was purified by flash column chromatography (9:1-3:2 hexanes:EtOAc, Rf = 0.22 in 1:1 hexanes:EtOAc) yielding Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester (103 mg, 31 mmol, 9.9%) as a yellow syrup.

Propanoic acid, 2-[bis(2,2,2-trifluoroethoxy)phosphinyl]-, methyl ester 준비 용품 및 원자재