Hydrochloric Acid → HCID 86673324, compound

Participants

Reaction Conditions

Reaction Steps

3-Furfural (0.96 g, 10 mmol) was dissolved in toluene (10 mL), N,N′-dimethylethylenediamine (1.08 mL, 10.0 mmol) and p-toluenesulfonic acid monohydrate (10 mg, 0.11 mmol) were added, and the mixture was stirred at 105° C. overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and 5% aqueous sodium hydrogen carbonate solution. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was dissolved in tetrahydrofuran (20 mL), 1.54N n-butyllithium/hexane solution (3 mL) was added dropwise at −78° C., and the mixture was stirred for 1 hour. Dry ice was added to the reaction mixture, and the mixture was stirred at room temperature for 2 hour. The solvent was evaporated under reduced pressure, N,N-dimethylformamide (10 mL), potassium carbonate (0.55 g, 4.0 mmol), and benzyl bromide (2.04 g, 11.9 mmol) were added to the obtained residue, and the mixture was stirred at 60° C. overnight. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound (0.33 g).

Provenance & Evidence