Sodium bis(2-methoxyethoxy)aluminiumhydride → 4-(1-ethyl-1-{4-[(E)-2-(1-hydroxy-cyclopentyl)-vinyl]-3-methyl-phenyl}-propyl)-2-methyl-phenol

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Reaction Steps

Sodium bis(2-methoxyethoxy)aluminum hydride (3.33 M solution in toluene, 6.7 mL, 22.3 mmol) was added to a solution of 4-{1-ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-phenol (Example 32-(1); 2.8 g, 7.4 mmol) in tetrahydrofuran (37 mL) at 0° C., and the mixture was stirred at the same temperature for four hours. The reaction mixture was diluted with ethyl acetate. Brine and celite were added, and the mixture was stirred at room temperature for 30 minutes. The organic layer was dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane only to hexane/ethyl acetate=3/1) to give the title compound (2.6 g, 92%).

Provenance & Evidence