Hydrochloric Acid → (S)-methyl 2-(6-((4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate

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Reaction Steps

(S)-Methyl 2-(6-((4′-((tert-butyldimethylsilyl)oxy)-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3 g (1.28 g, 2.40 mmol) was dissolved in 50 mL of tetrahydrofuran, followed by addition of 10 mL of 6 M hydrochloric acid. The reaction solution was stirred at room temperature for 12 hours. The resulting solution was concentrated under reduced pressure and the residue was mixed with 100 mL of ethyl acetate. The organic phase was washed with water (20 mL×2) and saturated sodium chloride solution (20 mL) successively, dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure. The residue was mixed with 60 mL of methanol and 1 mL of concentrated sulfuric acid. The resulting solution was heated to 70° C. and stirred for 1.5 hours. The solution was concentrated under reduced pressure, mixed with 100 mL of ethyl acetate, washed with water (20 mL×2), dried with anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the residue was purified by elution system B to obtain the title compound (S)-methyl 2-(6-((4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy)-2,3-dihydrobenzofuran-3-yl)acetate 3 h (670 mg, yield 67.0%) as a colorless oil.

Provenance & Evidence