反应详情

Into a flask, were placed triphenylphosphine (2.9 g, 11 mmol) and 4-fluorophenyl bromide (2.2 g, 11 mmol) prepared from 4-fluorophenethyl alcohol, followed by adding and dissolving xylene (5 ml), heating under reflux for 10 hours, depositing and filtering off white crystals (4.6 g, 10 mmol) of 4-fluorophenethyltriphenylphosphonium bromide. After drying, the white crystals were dissolved in tetrahydrofuran (THF, 10 ml), followed by stirring under ice cooling, adding a hexane solution (1.6M, 6.1 ml) of n-butyl lithium dropwise; stirring at room temperature for 2 hours, adding THF (5 ml) solution of 4-pentylcyclohexylacetaldehyde (2.1 g, 11 mmol), further stirring for 5 hours, adding ether after the completion of reaction. After separating the deposited white crystals by filtration, the filtrate was concentrated under reduced pressure, purifying the resulting oily substance by means of silica gel column chromatography, to obtain a mixture (2.2 g, 7.3 mmol) of 1-(4-fluorophenyl)-4-(4pentylcyclohexyl)-2Z-butene with its E-isomer.

1. customInto a flask, were placed
2. additionby adding
3. temperatureheating
4. temperatureunder reflux for 10 hours
5. customAfter drying
6. dissolutionthe white crystals were dissolved in tetrahydrofuran (THF, 10 ml)
7. additionadding a hexane solution (1.6M, 6.1 ml) of n-butyl lithium dropwise
8. stirringstirring at room temperature for 2 hours
9. stirringfurther stirring for 5 hours
10. customafter the completion of reaction
11. customAfter separating the deposited white crystals
12. filtrationby filtration
13. concentrationthe filtrate was concentrated under reduced pressure
14. custompurifying the resulting oily substance by means of silica gel column chromatography