Potassium Hydroxide → 7-(2-Furyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one

Participants

Reaction Conditions

Reaction Steps

In a mixture of ethanol (30 ml) and toluene (90 ml) was dissolved 1-amino-5-(2-furyl)cyclohexen-3-one (1.25 g), and to the solution were added 3-oxobutylaldehydedimethylacetal (2.36 g) and granulated potassium hydroxide (390 mg). The mixture was stirred at 115° C. (bath temperature), and to the mixture was added granulated potassium hydroxide (80 mg), 30 minutes later; 1 hour later; and 1.5 hours later; respectively. The reaction solution was stirred at the same temperature for 1 hour. The reaction solution was cooled, and concentrated under reduced pressure, and to the residue was added ethyl acetate (50 ml) and water (15 ml). The mixture was shaken and the separated upper layer was washed with saturated brine. Under reduced pressure, ethyl acetate was evaporated, and the residue was purified with silica gel column chromatography (EtOAc/hexane) and eluted with ethyl acetate/hexane to give 7-(2-furyl)-4-methyl-5,6,7,8-tetrahydroquinolin-5-one (1.0 g) as colorless crystals.

Provenance & Evidence