Ethyl Acetate → 3-(2-Phenyl-6-trifluoromethylquinolin-3-yl)propan-1-ol

Participants

Reaction Steps

0.50 g (1.50 mmol) of 5-phenyl-9-trifluoromethyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline 3 was dissolved in THF (15 ml), 1.65 g (3.00 mmol, 2 eq) of cerium(IV) ammonium nitrate were added at RT, and stirring was continued overnight at RT. When the reaction was complete, 50 ml of ethyl acetate were added, and the mixture was extracted 2× with 50 ml of water. The org. phase was dried and evaporated to dryness. The residue was recrystallised from ethyl acetate/diethyl ether, giving a pale-yellow solid (compound 4).

Provenance & Evidence