Tributylphosphine → Methyl (4'-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1'-biphenyl-4-yl)acetate

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Reaction Steps

1,1′-(Azodicarbonyl)dipiperidine (3.10 g, 12.3 mmol) and tri-n-butylphosphine (3.10 ml, 12.4 mmol) were successively added to a solution of [2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)phenyl]methanol (3.20 g, 10.3 mmol) obtained in Example (6-6) and methyl (4′-hydroxy-1,1′-biphenyl-4-yl)acetate (2.50 g, 10.3 mmol) obtained in Example (6-2) in tetrahydrofuran (40 ml) and the mixture was stirred at room temperature for 5 hours. After the formed white precipitate was removed by filtration, the precipitate was washed with ethyl acetate. After the filtrate was poured into water and the mixture was extracted with ethyl acetate (three times), the organic layer was successively washed with a 3N aqueous sodium hydroxide solution, water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=4/1) to give methyl (4′-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetate (3.16 g, yield: 58%).

Provenance & Evidence