反应详情

温度

0 °C

To a solution of 5-chloro-2-(2-(trifluoromethyl)phenyl)quinoline-3-carbaldehyde (2.1673 g, 6.456 mmol) in 32 mL of THF at 0° C. was added sodium borohydride (0.3664 g, 9.684 mmol) and the mixture was stirred at 0° C. After 1 hr at 0° C., the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL), and the organic layer was washed with brine (50 mL×3), dried over Na2SO4, filtered, and concentrated under reduced pressure to give (5-chloro-2-(2-(trifluoromethyl)phenyl)quinolin-3-yl)methanol as a yellow syrup: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.68-8.73 (1 H, m), 7.96-8.02 (1 H, m), 7.90-7.95 (1 H, m), 7.83-7.87 (1 H, m), 7.68-7.83 (3 H, m), 7.50-7.58 (1 H, m), 5.63 (1 H, t, J=5.3 Hz), 4.36 (2 H, br. s.); LC-MS (ESI) m/z 338.0 [M+H]+. The product was carried on crude without purification for the next step.

1. customthe mixture was partitioned between EtOAc (100 mL) and H2O (100 mL)
2. washthe organic layer was washed with brine (50 mL×3)
3. dry with materialdried over Na2SO4
4. filtrationfiltered
5. concentrationconcentrated under reduced pressure