Diethyl Ether → 1-(5-Chloro-3-(3-fluorophenyl)quinoxalin-2-yl)ethanol

Participants

Reaction Steps

To a stirring heterogeneous mixture of 5-chloro-3-(3-fluorophenyl)quinoxaline-2-carbaldehyde (0.4405 g, 1.537 mmol) in THF (14.95 mL, 1.537 mmol) was added methylmagnesium bromide 3 M in diethyl ether (1.024 mL, 3.073 mmol) dropwise at 0° C. and the mixture was then allowed to warm to room temperature. After 3 h, the reaction was quenched with saturated aq. NH4Cl (50 mL) and extracted with EtOAc (50 mL×2). The combined organic layers were washed with water (50 mL×1), brine (50 mL×1), dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography on a 40 g of Redi-Sep™ column using 0 to 50% gradient of EtOAc in hexane over 14 min and then 50% isocratic of EtOAc for 10 min as eluent to give 1-(5-chloro-3-(3-fluorophenyl)quinoxalin-2-yl)ethanol as a solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 8.14 (1H, dd, J=8.4, 1.2 Hz), 8.06 (1H, dd, J=7.6, 1.4 Hz), 7.87 (1H, dd, J=8.4, 7.6 Hz), 7.56-7.71 (3H, m), 7.37-7.46 (1H, m), 5.50 (1H, d, J=6.1 Hz), 5.04-5.13 (1H, m), 1.48 (3H, d, J=6.3 Hz); LC-MS (ESI) m/z 303.1 [M+H]+.

Provenance & Evidence