反应详情

温度

-78 °C

To a cold (−78° C.) anhydrous THF solution of 2-methoxy-6-bromoquinoline (1.16 g, 4.89 mmol) was added w-BuLi (2.05 mL of a 2.5 M solution in hexane, 5.13 mmol). The mixture was stirred at −78° C. under a nitrogen atmosphere for 15 min and 4-(trifluoromethyl)cyclohexanone (0.81 g, 4.89 mmol) was added slowly to the reaction. After addition was complete, the bath was allowed to warm to room temperature. The reaction mixture was quenched with saturated NH4Cl (aq) and extracted with EtOAc/hexanes. The organic layer was dried over Na2SO4 and evaporated in vacuo and the resultant residue was purified by flash chromatography on silica gel using gradient elution (0% to 20% EtOAc/hexanes, 150 mL; 20% to 35% EtOAc/hexanes, 204 mL; 35% to 75% EtOAc/hexanes, 381 mL) to provide Isomer A as the faster-moving isomer and Isomer B as the slower-moving isomer.

1. additionAfter addition
2. temperatureto warm to room temperature
3. customThe reaction mixture was quenched with saturated NH4Cl (aq)
4. extractionextracted with EtOAc/hexanes
5. dry with materialThe organic layer was dried over Na2SO4
6. customevaporated in vacuo
7. customthe resultant residue was purified by flash chromatography on silica gel using gradient elution (0% to 20% EtOAc/hexanes, 150 mL; 20% to 35% EtOAc/hexanes, 204 mL; 35% to 75% EtOAc/hexanes, 381 mL)
8. customto provide Isomer A as the faster-moving isomer and Isomer B as the slower-moving isomer