Hydride → (3-Methanesulfonyl-4-phenyl-quinolin-6-yl)-methanol

Participants

Reaction Conditions

Reaction Steps

3-Methanesulfonyl-4-phenyl-quinoline-6-carboxylic acid ethyl ester (example 61g, 100 mg, 0.28 mmol) in anhydrous tetrahydrofuran (8 mL) was cooled to 0° C. First portion of diisobutylaminum hydride in THF (1 M, 930 uL, 0.93 mmol) was added to the above mixture, and the reaction went for 1 hr at about room temperature. Then the reaction was cooled to 0° C., and second portion of diisobutylaluminum hydride in THF (1 M, 930 uL, 0.93 mmol) was added. The reaction continued for another 45 min at about room temperature. The completion of the reaction was monitored using LC-MS. Additional portion of diisobutylaluminum hydride in THF (1 M, 620 uL, 0.62 mmol) was added, and the reaction went for another 30 min. The reaction was quenched with saturated sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic solution was filtered through a bed of celit with ethyl acetate. The filtrate was collected, washed with water, brain, dried over sodium sulfate, filtered, and then concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 70-230 mesh, 60% ethyl acetate in hexane in 10 min, then 60%-100% ethyl acetate in hexane in 13 min) afforded (3-methanesulfonyl-4-phenyl-quinolin-6-yl)-methanol (70 mg, 79%). LC-MS m/e 314 (MH+).

Provenance & Evidence