反应详情

In a nitrogen atmosphere, a hexane solution of n-butyllithium (40 ml, 61.6 mmol) was added dropwise to a solution of fluorene (10.1 g, 60.8 mmol) in THF (300 ml) with ice cooling. The mixture was stirred at room temperature for 5 hours (resulting in a dark brown solution). The solution was ice cooled again, and a solution of 3-tert-butyl-1,6,6-trimethylfulvene (11.7 g, 66.5 mmol) in THF (300 ml) was added thereto dropwise in a nitrogen atmosphere. The reaction solution was stirred at room temperature for 14 hours. The resultant brown solution was ice cooled, and water (200 ml) was added. The obtained solution was extracted with diethyl ether. Then the organic phase was separated therefrom, and dried over magnesium sulfate. The organic phase was filtered, and the solvent was removed from the filtrate under reduced pressure, resulting in an orange-brown oil. The oil was purified by silica gel column chromatography (developing solvent: hexane) to give 3.8 g of a yellow oil. The analytical data are given below.

1. customresulting in a dark brown solution)
2. temperaturecooled again
3. stirringThe reaction solution was stirred at room temperature for 14 hours
4. temperaturecooled
5. extractionThe obtained solution was extracted with diethyl ether
6. customThen the organic phase was separated
7. dry with materialdried over magnesium sulfate
8. filtrationThe organic phase was filtered
9. customthe solvent was removed from the filtrate under reduced pressure
10. customresulting in an orange-brown oil
11. customThe oil was purified by silica gel column chromatography (developing solvent: hexane)