Diisobutylaluminum hydride → [8-Chloro-2-(pyridin-3-yl)quinolin-3-yl]methanol

Participants

Reaction Steps

To a suspension of 8-chloro-2-(pyridin-3-yl)quinoline-3-carboxylic acid ethyl ester (1.0 g, 3.2 mmol) in toluene at −78° C. was added a solution of DIBAL-H (10 mL, 1M in DCM) dropwise over 10 minutes. The mixture was stirred at this temperature for 2 h, then quenched by the addition of a saturated aqueous solution of Rochelle salt (5 mL). After warming to room temperature, extra Rochelle salt solution (5 mL) was added. The resulting solid was filtered, washed on the sinter with aqueous NaOH solution (2N) and water, and dried to give [8-chloro-2-(pyridin-3-yl)quinolin-3-yl]methanol (860 mg, quantitative) as a beige solid. δH (DMSO-d6) 8.92 (d, J 1.7 Hz, 1H), 8.73 (dd, J 4.8, 1.6 Hz, 1H), 8.61 (s, 1H), 8.17 (dt, J 7.9, 1.9 Hz, 1H), 8.09 (dd, J 8.2, 1.1 Hz, 1H), 7.97 (dd, J 7.5, 1.2 Hz, 1H), 7.63 (m, 1H), 7.58 (ddd, J 7.8, 4.8, 0.6 Hz, 1H), 5.76 (s, 1H), 5.62 (t, J 5.2 Hz, 1H), 4.68 (d, J 4.9 Hz, 2H). LCMS (ES+) 271.0 (M+H)+.

Provenance & Evidence