Toluene → 7-Quinolinemethanol

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

Methyl quinoline-7-carboxylate (5 g, 0.01 mol) was dissolved in tetrahydrofuran (40 mL) at −20° C. under an atmosphere of nitrogen. 60% REDAL (60:40, Red-Al(R):toluene, 6.53 mL, 0.0201 mol) was added and allowed to stir at −20° C. for 4 hours. After warming to room temperature, the reaction was quenched slowly with water, concentrated under reduced pressure, partitioned between EtOAc and water, and filtered through Celite. The aqueous phase was extracted with EtOAc. The combined organic layers were dried with MgSO4, and concentrated under reduced pressure. The residue was purified by silica gel column to afford the title compound.

Herkunft & Nachweise