Tetrahydrofuran → 6-Fluoro-8-(3-methoxypropoxy)-2-methylquinoline

Participants

Reaction Conditions

Reaction Steps

Triphenylphosphine (0.74 g, 2.8 mmol) was dissolved in tetrahydrofuran (0.94 mL, 1.1 mmol) and diisopropyl azodicarboxylate (0.35 mL, 1.8 mmol), 3-methoxypropan-1-ol (0.14 mL, 1.5 mmol) and 6-fluoro-2-methylquinolin-8-ol (0.20 g, 1.1 mmol) were added. The vessel was sealed and the mixture was stirred at 50° C. for 12 hours. The cooled reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by normal phase chromatography on silica gel (10-50% ethyl acetate/hexanes) to provide the title compound (0.22 g, 77%).

Provenance & Evidence