Sodium Carbonate → (E)-2-[4-(3-Benzyloxy-propylsulfanyl)-phenyl]-3-cyclopentyl-acrylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

Add potassium acetate (1.7 g, 17.3 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2′]bi[[1,3,2]dioxaborolanyl] (1.6 g, 6.35 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (424 mg, 0.58 mmol) to a solution of 1-(3-benzyloxy-propylsulfanyl)-4-bromo-benzene (1.95 g, 5.77 mmol) in 15 mL DMF and stir 1 hour at 80° C. Then add (Z)-2-bromo-3-cyclopentyl-acrylic acid ethyl ester (2.85 g, 11.54 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (424 mg, 0.58 mmol) and sodium carbonate solution (2 M, 14.0 mL, 28.0 mmol) and stir at 80° C. over night. Add 100 mL ethyl acetate and filter. Wash with water and brine, filter through a hydrophobic filter paper and concentrate. Further purification via silica gel column chromatography, eluting with dichloromethane affords the title compound as yellow oil (4.37 g). MS (m/e): 425 (M+H).

Provenance & Evidence