反应详情

After p-toluenesulfonic acid monohydrate (1.01 g, 5.31 mmol) was added to a solution of methyl (4′-{[2-(dimethoxymethyl)-3-(methoxymethoxy)-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetate (2.38 g, 4.45 mmol) obtained in Example (6-7) in acetone (14 ml), the mixture was stirred at room temperature for 14 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, 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. Potassium carbonate (738 mg, 5.34 mmol) and allyl bromide (0.462 ml, 5.34 mmol) were successively added to a solution of the obtained residue in N,N-dimethylformamide (4 ml) and the mixture was stirred at 50° C. for 2 hours. After the reaction mixture was poured into water and the mixture was extracted with ethyl acetate, the organic layer was successively washed with water and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=50/1-2/1) to give methyl (4′-{[3-(allyloxy)-2-formyl-4-(trifluoromethyl)benzyl]oxy}-1,1′-biphenyl-4-yl)acetate (1.81 g, yield: 84%).

1. extractionthe mixture was extracted with ethyl acetate
2. washthe organic layer was successively washed with water
3. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
4. customThe solvent was removed under reduced pressure
5. customto give a residue
6. stirringthe mixture was stirred at 50° C. for 2 hours
7. extractionthe mixture was extracted with ethyl acetate
8. washthe organic layer was successively washed with water
9. dry with materiala saturated aqueous NaCl solution and dried with anhydrous sodium sulfate
10. customThe residue obtained
11. customby removing the solvent under reduced pressure
12. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=50/1-2/1)