Ethylene Glycol → 3-[2-(4-bromophenyl)-1,3-dioxolan-2-yl]-N,N-diethylpropan-1-amine

Participants

Reaction Conditions

Reaction Steps

Ethylene glycol (10 mL) and p-toluenesulfonic acid monohydrate (128 mg) were added to a solution of 1-(4-bromophenyl)-4-(diethylamino)butan-1-one (2.0 g) in toluene (80 mL), and the mixture was stirred at 150° C. for one hour. The reaction solution was cooled to room temperature and p-toluenesulfonic acid monohydrate (1.28 g) was added, after which the mixture was stirred at 150° C. for further one hour. The reaction solution was cooled to room temperature and neutralized with saturated aqueous sodium bicarbonate, followed by extraction with chloroform. The organic layer was dried over anhydrous magnesium sulfate and filtered. The solvent was then evaporated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=10:1) to give the title compound as a brown oil (2.09 g, 91%).

Provenance & Evidence