Lithium Hydroxide → 4-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid

Participants

Reaction Conditions

Reaction Steps

To an ambient temperature solution of 4-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-2-methyl-benzoic acid methyl ester (2.40 g, 5.73 mmol) in dioxane/water (30/30 ml) is added lithium hydroxide (412 mg, 17.20 mmol) and heated to 60° C. for 1 h. The reaction is concentrated and partitioned between Et2O/EtOAc (150/150 ml) and 1N HCl (50 ml). The aqueous phase is extracted with a second portion of EtOAc (100 ml) and the combined organic phases are washed with water (50 ml), brine (50 ml), dried (MgSO4) and concentrated to yield the title compound (1.57 g, 68%).

Provenance & Evidence