Ethyl Acetate → 1-(2-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenyl}-(E)-vinyl)-cycloheptanol

Participants

Reaction Conditions

Reaction Steps

Sodium bis(2-methoxyethoxy)aluminum hydride (65 wt % solution in toluene, 1.4 mL, 4.66 mmol) was added to a solution of 1-{4-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-2-methyl-phenylethynyl}-cycloheptanol (Example 128-(1); 624 mg, 1.54 mmol) in tetrahydrofuran (7.5 mL) in a nitrogen atmosphere at 0° C., and the mixture was stirred at 0° C. for two hours. Brine and ethyl acetate were added to the reaction mixture, which was stirred for 20 minutes. Then, celite was added and the mixture was further stirred for 30 minutes. The mixture was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=90:10 to 50:50) to give the target compound as a colorless oil (629 mg, 100%).

Provenance & Evidence