HCID 86609128, compound → HCID 86609127, compound

Participants

Reaction Steps

To a solution of (2R)-2-[(3-allyl-2′,6′-dichlorobiphenyl-2-yl)oxy]but-3-en-1-yl 4-methylbenzenesulfonate (702 mg, 1.394 mmol) in anhydrous dichloromethane (35 mL) at room temperature under nitrogen was added benzylidene-bis(tricyclohexylphosphine)dichlororuthenium (114 mg, 0.1394 mmol) and the reaction mixture stirred at room temperature for 5 hours. The reaction mixture was then concentrated under reduced pressure to afford a brown syrup. The crude product was dissolved in ethyl acetate (7 mL) and the solution added to a suspension of platinum (IV) oxide (32 mg, 0.139 mmol) in absolute ethanol (21 mL). The mixture was then hydrogenated at 12 psi of hydrogen for 1 hour. The reaction mixture was filtered through celite and the filtrate concentrated under reduced pressure to afford a brown syrup. Purification by flash chromatography using a solvent gradient of 3 to 10% ethyl acetate in hexane afforded 0.615 g (92%) of [(2R)-9-(2,6-dichlorophenyl)-2,3,4,5-tetrahydro-1-benzoxepin-2-yl]methyl 4-methylbenzenesulfonate as a yellow solid. MS (ESI) m/z 477 ([M+H]+).

Provenance & Evidence