Triethylamine → HCID 22493475, compound

Participants

Reaction Steps

A 1-L, 3-necked round-bottom flask was equipped with a magnetic stirring bar, a condenser with a nitrogen inlet, and two stoppers. The vessel was charged with 3-bromobenzaldehyde (18.5 g), 3-butyn-1-ol (10.5 g), triethylamine (100 mL), and THF (100 mL). To this mixture was then added PdCl2 (PPh3)2 (1.4 g) and CuBrMe2S (0.405 g). The reaction mixture was heated to reflux using a heating mantle. After 4 h when TLC showed complete consumption of the bromide, the mixture was allowed to cool to room temperature, transferred to a 1-L round-bottom flask and concentrated under reduced pressure. The residue was dissolved in 250 mL of ethyl acetate. The solution was washed with water and brine, dried over MgSO4, and filtered. The solvents were removed from the filtrate under reduced pressure to obtain the title compound as pale yellow oil (16.8 g).

Provenance & Evidence