Ethyl Acetate → (2S)-2-{3-[4-(Methylsulfonyl)phenoxy]-5-[5-(1,3-thiazol-2-yl)-1H-pyrrol-2-yl]phenoxy}propan-1-ol

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Reaction Steps

Under nitrogen atmosphere, 2-(5-{3-[(1S)-2-methoxy-1-methylethoxy]-5-[4-(methylsulfonyl)phenoxy]phenyl}-1H-pyrrol-2-yl)-1,3-thiazole (88.8 mg, 0.183 mmol) synthesized in Example (1i) was dissolved in dichloromethane (5 mL), and a boron tribromide/dichloromethane solution (1.0M, 220 μL, 0.22 mmol) was added at −78° C. Subsequently, the temperature was brought back to room temperature, followed by stirring for 30 minutes. A saturated aqueous sodium hydrogencarbonate solution was added to the reaction solution, and extraction was carried out with ethyl acetate. The organic layer was washed with saturated brine, and subsequently dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-50%) to afford the desired compound (52.2 mg, yield 61%) as a pale yellow solid.

Provenance & Evidence