Potassium Hydroxide → HCID 18317648, compound

Participants

Reaction Conditions

Reaction Steps

In a mixture of ethanol (30 ml) and toluene (90 ml) was dissolved 1-amino-5-(5-methyl-2-thienyl)cyclohexen-3-one (1.66 g). To the solution were added 3-oxobutylaldehydedimethylacetal (2.6 g) and granulated potassium hydroxide (430 mg), and the mixture was stirred at 115° C. (bath temperature). To the mixture were added granulated potassium hydroxide (80 mg), 30 minutes later; 1 hour later; 1.5 hours later; respectively. The reaction solution was stirred at the same temperature for 1 hour and cooled. Under reduced pressure, the solvent was evaporated, and to the residue were added ethyl acetate (50 ml) and water (10 ml). The mixture was shaken, and the separated upper layer was washed with saturated brine and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (EtOAc/hexane) and eluted with ethyl acetate/hexane to give 4-methyl-7-(5-methyl-2-thienyl)-5,6,7,8-tetrahydroquinolin-5-one (1.78 g) as pale yellow oil.

Provenance & Evidence