Cesium fluoride → (1RS,2SR,6RS,7SR)-4-(4'-chloro-4-ethyl-2'-fluorobiphen-3-yl)-1,7-dimethyl-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione

Participants

Reaction Steps

A mixture of (1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione (113 mg, 0.3 mmol), 4-chloro-2-fluorophenylboronic acid (103 mg, 0.6 mmol) and cesium fluoride (449 mg, 3.0 mmol) in degassed 1,2-dimethoxyethane (1.5 ml) are stirred under nitrogen at room temperature for 40 minutes. [1,1′-bis(diphenylphosphino) ferrocene]dichloropalladium(II) complex with dichloromethane (48 mg, 0.06 mmol) is added, followed by a further quantity of 1,2-dimethoxyethane (1 ml) and reaction mixture is heated to 80° C. for 18 hours. The mixture is cooled to room temperature, then diluted with dichloromethane and filtered through a small plug of diatomaceous earth. The filtrate is evaporated and the residue is purified by column chromatography on silica gel, to give (1RS,2SR,6RS,7SR)-4-(4′-chloro-4-ethyl-2′-fluorobiphen-3-yl)-1,7-dimethyl-10-oxatricyclo-[5.2.1.02,6]decane-3,5-dione.

Provenance & Evidence