Potassium Hydroxide → HCID 57443478, compound

Participants

Reaction Conditions

Reaction Steps

A 1 N potassium hydroxide aqueous solution (2 mL) was added to a solution of (E)-3-{5-[4-(1-{4-[3-(t-butyl-dimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-furan-2-yl}-acrylic acid ethyl ester (Example 5-(1); 42 mg, 0.065 mmol) in methanol (2 mL) and tetrahydrofuran (2 mL) at room temperature, and the mixture was stirred at 60° C. for two hours. The reaction mixture was concentrated under reduced pressure, and ethyl acetate and a saturated aqueous potassium bisulfate solution were added to the residue. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (0.2 mL). A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (2 mL, 2 mmol) was added at room temperature, and the mixture was stirred at 65° C. for one hour. A potassium bisulfate aqueous solution and ethyl acetate were added to the reaction mixture to separate the layers. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC (hexane/ethyl acetate=1/2) to give the title compound (21.2 mg, 65%).

Provenance & Evidence