Tetrahydrofuran → (2-(3-Fluorophenyl)-8-methoxyquinolin-3-yl)methanol

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-(3-fluorophenyl)-8-methoxyquinoline-3-carbaldehyde (2.2967 g, 8.165 mmol) in tetrahydrofuran (40.83 mL, 8.165 mmol) at 0° C. was added sodium borohydride (0.4634 g, 12.25 mmol) and the mixture was stirred at 0° C. After 1 h of stirring at 0° C., the mixture was partitioned between EtOAc (100 mL) and H2O (100 mL), and the organic layer was washed with brine (100 mL×2), dried over Na2SO4, filtered, and concentrated under reduced pressure to give (2-(3-fluorophenyl)-8-methoxyquinolin-3-yl)methanol as a brown solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.43 (1H, s), 7.46-7.60 (5H, m), 7.29-7.36 (1H, m), 7.19 (1H, dd, J=7.4, 1.6 Hz), 5.50 (1H, t, J=5.3 Hz), 4.61 (2H, dd, J=5.5, 0.8 Hz), 3.96 (3H, s); LC-MS (ESI) m/z 284.0 [M+H]+. The brown solid was carried on crude without purification for the next step.

Provenance & Evidence