反应详情

In a 200 ml three-necked flask equipped with a magnetic stirrer chip and three-way cock thoroughly purged with nitrogen, 0.65 g of powdery potassium hydroxide (13.0 mmol) and 70 ml of dehydrated dimethoxy ethane were added in a nitrogen atmosphere. To the suspension, 1.24 g of 3-tert-butyl-1-methyl-cyclopentadiene (9.11 mmol) was added dropwise at room temperature and then 2.40 g of 4,4′-dichloro-benzophenone (9.58 mmol) was added and stirred under reflux for 3 days. To a 30 ml of a hydrochloric acid aqueous solution (1N) set in an ice bath, the reaction mixture was gradually added dropwise and stirred for some time. Diethyl ether was added to the mixed solution to separate an organic phase. The organic phase was washed with a saturated sodium bicarbonate aqueous solution, water and saturated brine. The organic phase was dried with anhydrous magnesium sulfate, thereafter the drying agent was filtered off and the solvent was distilled off from the filtrate under reduced pressure to give a reddish-orange solid. The solid was purified with a column chromatography using 110 g of silica gel (developing solvent: n-hexane) and the developing solvent was distilled off under reduced pressure, and thereby the aimed compound was obtained in an amount of 2.79 g (7.56 mmol) as a red solid (yield: 83%).

1. customIn a 200 ml three-necked flask equipped with a magnetic stirrer chip and three-way cock
2. additionwere added in a nitrogen atmosphere
3. temperatureunder reflux for 3 days
4. additionthe reaction mixture was gradually added dropwise
5. stirringstirred for some time
6. customto separate an organic phase
7. washThe organic phase was washed with a saturated sodium bicarbonate aqueous solution, water and saturated brine
8. dry with materialThe organic phase was dried with anhydrous magnesium sulfate
9. filtrationthe drying agent was filtered off
10. distillationthe solvent was distilled off from the filtrate under reduced pressure
11. customto give a reddish-orange solid
12. customThe solid was purified with a column chromatography
13. distillationthe developing solvent was distilled off under reduced pressure