Sodium Chloride → 6-Hydroxymethylquinoline

Participants

Reaction Conditions

Reaction Steps

59.5 g (0.296 mole) of ethyl quinoline-6-carboxylate are stirred in 970 ml of ether at -70° C. with 750 ml (0.9 mole) of diisobutylaluminum hydride (DIBAL, 20% strength in toluene, 1.2 molar) overnight. The temperature is then allowed to rise to -35° C. and 310 ml of sodium chloride solution are added, whereupon the temperature slowly comes to 20° C. The mixture is stirred at 20° C. for 3 hours and the aluminum hydroxide is filtered off with suction and rinsed with ether/ethyl acetate. The organic phase is washed with 100 ml of sodium chloride solution, dried over Na2SO4 and evaporated. Crude yield: 40 g

Provenance & Evidence