Dimethylformamide → HCID 18509522, compound

Participants

Reaction Steps

N-(3-bromo-5-methylbenzyl)methylamine (2.68 g; 12.5 mmol) and sodium carbonate (1.89 g; 17.9 mmol) were added to N,N-dimethylformamide (20 ml). While the mixture was stirred at room temperature, 1-bromo-6,6-dimethyl-2-hepten-4-yne (2.40 g; 11.9 mmol) in N,N-dimethylformamide (15 ml) was added dropwise. The mixture was stirred at room temperature for 1.5 hours, and reaction was stopped by pouring the mixture into ice+saturated aqueous sodium bicarbonate solution, followed by extraction with ethyl acetate (100 ml). The organic layer was washed with saturated aqueous sodium bicarbonate solution and with saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=15:1), to thereby yield 2.24 g of the target compound (yield: 56.3%).

Provenance & Evidence