Iodine → HCID 58535467, compound

Participants

Reaction Conditions

Reaction Steps

THF (5 ml) was added to magnesium turnings (0.30 g) in a reaction vessel under an atmosphere of nitrogen, and a minute amount of iodine was added. 4-(2-Bromoethyl)-4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl (29) (4.60 g) in a THF (5 ml) solution was slowly added dropwise at a temperature 50° C. or lower. After the addition had been completed, the stirring was continued at room temperature for 30 minutes. The reaction mixture was then cooled to −30° C. or lower, and 5-(4-propylcyclohexyl)tetrahydro-2H-pyran-2-one (20) (2.46 g) in a THF (5 ml) solution was added dropwise. After the reaction mixture had been stirred at room temperature for 5 hours, it was quenched with a saturated aqueous solution of ammonium chloride, and water (20 ml) was added to give two layers. The water layer was extracted with toluene (10 ml) twice, and the combined organic layer was washed with water and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (silica gel: 20 g, eluent: toluene/ethyl acetate=70/30 by volume) to give 2-(2-(4′-ethoxy-2,2′,3,3′-tetrafluorobiphenyl-4-yl)ethyl)-5-(4-propylcyclohexyl)tetrahydro-2H-pyran-2-ol (30) (2.7 g) in 47.1% yield.

Provenance & Evidence