Triethylamine → 1-Ethynyl-2-methoxybenzene

2-Iodoanisole (10.5 g) andtrimethylsilylacetylene (10.3 g) were reacted in dimethylformamide (50 ml), in the presence of dichloro-bis-triphenylphosphine palladium (1.0 g), cuprous iodide (0.5 g) and triethylamine (15 ml) in nitrogen atmosphere at 50° C. for 12 hr. The resulting reaction solution was evaporated, and to the resulting residue were added ethyl acetate and water. The resulting organic layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was dissolved in methanol (100 ml), a 5N aqueous solution of sodium hydroxide (20 ml) was added thereto, and then reacted at 60° C. for 1 hr. The reaction solution was evaporated, and to the resulting residue were added ether and water. The resulting ether layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system) to give the title compound as a pale yellow oil (3.02 g, yield; 51%).

1. customThe resulting reaction solution
2. customwas evaporated
3. additionto the resulting residue were added ethyl acetate and water
4. washThe resulting organic layer was washed with water and brine
5. dry with materialdried over magnesium sulfate
6. customThe solvent was evaporated
7. dissolutionthe resulting residue was dissolved in methanol (100 ml)
8. additiona 5N aqueous solution of sodium hydroxide (20 ml) was added
9. customreacted at 60° C. for 1 hr
10. customThe reaction solution was evaporated
11. additionto the resulting residue were added ether and water
12. washThe resulting ether layer was washed with water and brine
13. dry with materialdried over magnesium sulfate
14. customThe solvent was evaporated
15. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

ORD-Eintrag

ord-9a7e89174b31447a968debd35d5eaad8

Quelldatensatz

uspto-grants-2004_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06790844B2