HCID 86609103, compound → HCID 86609102, compound

Participants

Reaction Steps

To a solution of (2R)-2-({2′,6′-dichloro-3-[(1E)-prop-1-enyl]-1,1′-biphenyl-2-yl}oxy)but-3-enyl 4-methylbenzenesulfonate (2.02 g, 4.01 mmol) in anhydrous dichloroethane (50 mL) at room temperature under nitrogen was added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (0.33 g, 0.401 mmol) and the reaction mixture stirred at room temperature for 20 hours and then heated to 50° C. for 45 hours. The cooled reaction mixture was concentrated to a small volume under reduced pressure and then directly pre-adsorbed onto silica gel. Purification by flash chromatography using a solvent gradient of 5 to 15% ethyl acetate in hexane afforded 1.52 g (82%) of [(2R)-8-(2,6-dichlorophenyl)-2H-chromen-2-yl]methyl 4-methylbenzenesulfonate as a brown foam. MS (ESI) m/z 478 ([M+NH4]+).

Provenance & Evidence