Tributylphosphine → Ethyl 3-(4-{[2-(benzyloxy)benzyl]oxy}-3,5-difluorophenyl)propanoate

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2-(Benzyloxy)benzaldehyde (274 mg, 1.3 mmol) dissolved in methanol (20 mL), sodium borohydride (73 mg, 1.9 mmol) was added thereto, and then the mixture was stirred with ice cooling for 2 hours. To the reaction solution was added water, and the reaction mixture was extracted with ethyl acetate. The extract was dried, and then concentrated under reduced pressure. The residue was dissolved in tetrahydrofuran (10 mL). Ethyl 3-(3,5-difluoro-4-hydroxyphenyl)propanoate (200 mg, 0.86 mmol), tributylphosphine (0.23 mL, 1.1 mmol) and azodicarbonyldipiperidine (282 mg, 1.1 mmol) were added thereto, and the mixture was stirred at room temperature for 12 hours. The reaction solution was purified with alumina column chromatography (ethyl acetate) and silica gel column chromatography (hexane/ethyl acetate=100:0 to 80:20) to give the title compound (162 mg, yield 29%) as an oily matter.

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