Triethylamine → 4-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol

Participants

Reaction Conditions

Reaction Steps

Triethylamine (5.2 mL, 37.3 mmol), 1-ethynylcyclopentanol (2 g, 18.2 mmol), cuprous iodide (0.24 g, 1.26 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.44 g, 1.25 mmol) were added to a solution of trifluoromethanesulfonic acid 4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl ester (Example 1-(1); 5.2 g, 12.5 mmol) in acetonitrile (52 mL) in a nitrogen atmosphere at room temperature, and the mixture was stirred at 110° C. for four hours. Ethyl acetate was added to the residue. The organic layer was washed with water and brine and then dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=4/1) to give the title compound (3 g, 64%).

Provenance & Evidence