反应详情

n-Butyllithium (7.2 mL, 1.56 M hexane solution, 11.2 mmol) was added to a solution in THF (25 mL) of 1-bromo-4-(dimethoxymethyl)benzene (2.29 g, 9.91 mmol) at −78° C. The mixture was stirred at the same temperature for 2 hours, and then cyclopentanone (1.34 mL, 15.1 mmol) was added thereto. The resulting mixture was heated to room temperature and then stirred for 1 hour. The reaction was terminated by adding a saturated ammonium chloride aqueous solution, and an extraction with ethyl acetate was conducted three times. The resulting organic layers were washed with water and saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate, 5:1, v/v) to give an oily compound. Trifluoroacetic acid (9 mL) was added to a dichloromethane-water (9.1 mL, 100:1, v/v) mixture solution containing the resulting oily compound at room temperature, and the mixture was continuously stirred for 20 minutes. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate, 10:1, v/v) to give 1.18 g of the title compound (light brown crystalline solid, yield: 90%).

1. stirringstirred for 1 hour
2. customThe reaction was terminated
3. additionby adding a saturated ammonium chloride aqueous solution
4. extractionan extraction with ethyl acetate
5. washThe resulting organic layers were washed with water and saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customThe solvent was evaporated
8. customthe resulting residue was purified by silica gel column chromatography (hexane
9. customethyl acetate, 5:1, v/v) to give an oily compound
10. additionv/v) mixture solution containing the resulting oily compound at room temperature
11. stirringthe mixture was continuously stirred for 20 minutes
12. customThe solvent was evaporated
13. customthe resulting residue was purified by silica gel column chromatography (hexane