Water → HCID 86642715, compound

Participants

Reaction Conditions

Reaction Steps

71 mg (0.2 mmol) of 2-(dicyclohexylphosphino)biphenyl and 23 mg (0.1 mmol) of palladium acetate are added to a solution of 2 g (5.07 mmol) of methyl(E)-3-(2-benzyloxy-4-iodophenyl)acrylate, 1.1 ml (7.6 mmol) of triethylamine and 2.9 g (5.07 mmol) of 4-allyl-2-methoxyphenyl 1-butane-1-sulfonate in 20 ml of dimethylformamide. The reaction mixture is heated at 80° C. for 4 hours. The reaction is treated by addition of 50 ml of water and then extracted with ethyl acetate. The organic phases are combined, washed with saturated sodium chloride solution, dried over sodium sulfate and filtered, and the solvents are then evaporated off. The residue is purified by chromatography on a column of silica eluted with a 90/10 heptane/ethyl acetate mixture. 2.53 g (91%) of methyl(E)-3-(2-benzyloxy-4-{(E)-3-[4-(butane-1-sulfonyloxy)-3-methoxyphenyl]propenyl}phenyl)acrylate are obtained in the form of a yellow oil.

Provenance & Evidence