反应详情

Under a nitrogen atmosphere, to a mixture of 1-bromo-4-(6-methoxyhexyloxy)benzene (3.68 g), 2-methyl-3-butyn-2-ol (1.86 ml) and triethylamine (18 ml) in pyridine (7.4 ml) was added triphenylphosphine (67.2 mg), copper(I) iodide (24.4 mg) and dichlorobis(triphenylphosphine)palladium(II) (18.0 mg), and refluxed overnight. After cooling, insoluble material was filtered off and washed with isopropyl ether. The filtrate was evaporated under reduced pressure. To the residue was added isopropyl ether and the mixture was washed with 0.1N-hydrochloric acid, water and brine. The organic layer was dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure to give a crude yellow oil. The crude yellow oil was purified by silica gel chromatography (10:1-2:1 hexane-ethyl acetate) to give 4-[4-(6-methoxyhexyloxy)phenyl]-2-methyl-3-butyn-2-ol (3.17 g) as a yellow powder.

1. temperaturerefluxed overnight
2. temperatureAfter cooling
3. filtrationinsoluble material was filtered off
4. washwashed with isopropyl ether
5. customThe filtrate was evaporated under reduced pressure
6. additionTo the residue was added isopropyl ether
7. washthe mixture was washed with 0.1N-hydrochloric acid, water and brine
8. dry with materialThe organic layer was dried over magnesium sulfate
9. filtrationMagnesium sulfate was filtered off
10. customthe filtrate was evaporated under reduced pressure
11. customto give a crude yellow oil
12. customThe crude yellow oil was purified by silica gel chromatography (10:1-2:1 hexane-ethyl acetate)