1,4-Dioxane → HCID 54570789, compound

Participants

Reaction Conditions

Reaction Steps

3-(3-(diethoxyphosphoryl-4-trifluoromethanesulfonyloxy-pheny)-propionic acid methyl ester (1 g, 223 mmol) was dissolved in dry dioxane 25 mL together with vinyl tributyltin (0.67 mL, 229 mmol), LiCl (283 mg, 6.7 mmol), Pd(PPh3)2Cl2 (47 mg, 0.067 mmol) and a crystal of 2,6-di-tert-butyl-4-methylphenol. Reaction mixture was degassed with Argon and heated to 98° C. and stirred for 2 hrs. Reaction mixture was cooled to rt and diluted with excess ether and 10 mL saturated aqueous KF solution and stirred at rt overnight. The reaction mixture was filtered through celite and separated organic layer was washed with 1 N HCl, brine, dried Na2SO4 and concentrated. Brownish oil was purified by flash column chromatography (EtOAc/hexane 90:10, Rf=0.50) to give an oil 470 mg (yield 65%).

Provenance & Evidence