反应详情

To a stirred solution of 2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone (0.715 g, 2.77 mmol) in 1,4-dioxane (45 ml), and under an atmosphere of nitrogen, are added copper (II) chloride (0.743 g, 5.53 mmol) and lithium chloride (0.176 g, 4.15 mmol). The reaction is heated at reflux for 7 hours and allowed to cool to room temperature overnight. The remaining solid is removed by filtration and washed with ethyl acetate (50 ml). The filtrate is washed with water (2×25 ml) and the aqueous washings re-extracted with ethyl acetate (1.5 ml). The combined organic phases are washed with brine (15 ml), dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give a brown oil. The crude product is purified by column chromatography on silica gel to give 5-chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone.

1. temperatureThe reaction is heated
2. temperatureat reflux for 7 hours
3. customThe remaining solid is removed by filtration
4. washwashed with ethyl acetate (50 ml)
5. washThe filtrate is washed with water (2×25 ml)
6. extractionthe aqueous washings re-extracted with ethyl acetate (1.5 ml)
7. washThe combined organic phases are washed with brine (15 ml)
8. dry with materialdried over anhydrous magnesium sulfate
9. filtrationfiltered
10. customthe filtrate is evaporated under reduced pressure
11. customto give a brown oil
12. customThe crude product is purified by column chromatography on silica gel