Hydrochloric Acid → 2-(Allyloxy)-6-{[(4'-{[(allyloxy)carbonyl]methyl}-3-fluoro-1,1'-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoic acid

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Reaction Steps

After an aqueous solution (1.1 ml) of sodium chlorite (125 mg, 1.38 mmol) and sodium dihydrogenphosphate monohydrate (125 mg, 0.91 mmol) was added dropwise to a solution of allyl (4′-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-3′-fluoro-1,1′-biphenyl-4-yl)acetate obtained in Example (12-5) in a mixture of tert-butyl alcohol (2.4 ml), 1,4-dioxane (0.8 ml) and 2-methyl-2-butene (0.8 ml), the mixture was stirred at room temperature for 2 hours. After a 5% aqueous sodium thiosulfate solution was added to the reaction mixture, the mixture was poured into 1N hydrochloric acid and extracted with ethyl acetate (twice). The organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure to give a residue. The obtained residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate) to give 2-(allyloxy)-6-{[(4′-{[(allyloxy)carbonyl]methyl}-3-fluoro-1,1′-biphenyl-4-yl)oxy]methyl}-3-(trifluoromethyl)benzoic acid (135 mg, yield: 100%).

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