反应详情

温度

-78 °C

To a solution of 1-(4-bromo-2-iodophenoxy)-5-chloropentan-2-one (1.61 g, 3.86 mmol) in THF (35 mL) was added vinylmagnesium bromide (1M solution in THF, 4.3 mL) at −78° C. under an argon atmosphere. After stirring for 1 hour at −78° C., the mixture was gradually warmed up to −30° C. over 1 hour. The reaction was quenched by adding saturated aqueous NH4Cl solution and extracted with EtOAc. The combined organic layer were washed with brine, dried over Na2SO4, filtered, and the filtrate was evaporated. The residue was purified by silicagel column chromatography (EtOAc-hexane, a linear gradient of EtOAc from 0 to 20%) afforded 3-[(4-bromo-2-iodophenoxy)methyl]-6-chlorohex-1-en-3-ol (1.35 g).

1. temperaturethe mixture was gradually warmed up to −30° C. over 1 hour
2. customThe reaction was quenched
3. additionby adding saturated aqueous NH4Cl solution
4. extractionextracted with EtOAc
5. washThe combined organic layer were washed with brine
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. customthe filtrate was evaporated
9. customThe residue was purified by silicagel column chromatography (EtOAc-hexane