Acetone → (E)-3-Cyclohexyl-2-(4-methanesulfonyl-phenyl)-acrylic acid ethyl ester

Participants

Reaction Steps

Add a suspension of oxone ® (33 g, 53 mmol) in water (300 mL) to a solution of (E)-3-cyclohexyl-2-(4-methylsulfanyl-phenyl)-acrylic acid ethyl ester (7.4 g, 24 mmol) in acetone (300 mL). Stir for three h, and then add water. Extract the resulting mixture with dichloromethane (2×500 mL). Combine the extracts, wash them with saturated aqueous sodium chloride solution, dry them over magnesium sulfate, and remove solvent under vacuum. Apply the residue to silica gel column, and elute this with a 15:15:70 mixture of dichloromethane: ethyl acetate: hexane to afford the title compound as an off-white solid (7.35 g). MS (m/e): 337 (M+H).

Provenance & Evidence