Triethylamine → HCID 22493475, compound

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).

1. temperatureThe reaction mixture was heated
2. temperatureto reflux
3. customconsumption of the bromide
4. customtransferred to a 1-L round-bottom flask
5. concentrationconcentrated under reduced pressure
6. dissolutionThe residue was dissolved in 250 mL of ethyl acetate
7. washThe solution was washed with water and brine
8. dry with materialdried over MgSO4
9. filtrationfiltered
10. customThe solvents were removed from the filtrate under reduced pressure

ORD record

ord-a89f7b8a0ad84e36a1be600555cc8a5e

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06884803B2