反应详情

In a 1000 mL round flask, 2,9,9-trimethyl-2,3-dihydrocyclopenta[b]fluoren-1(9H)-one (50 g, 190.6 mmol) was dissolved THF 400 mL and ethanol 400 mL, and then stirred. Sodium borohydride (NaBH4) (9.4 g, 247.8 mmol) was added to the reaction product in five lots, and then stirred for 12 hours. The resultant mixture, after removal of solvent, was dissolved in ethylacetate, and then washed with water three times. The organic layer was dried over magnesium sulfate, followed by removal of volatile materials. The dried reaction product was dissolved in 320 mL of toluene, and then inputted to a 500 mL round flask. After that, p-toluene sulfonic acid (0.2 g) was inputted thereto, and then water was completely removed under reflux with Dean-Stark. The resultant material was cooled to room temperature, and then an aqueous ammonium chloride solution (150 mL) and 200 mL of diethyl ether were injected thereto, followed by separation of the organic layer. The organic layer collected by extracting the residue with diethyl ether was dried over magnesium sulfate, followed by removal of volatile materials, and then purified by using silica gel column chromatography, to thereby obtain 42.0 g of 2,9,9-trimethyl-3,9-dihydrocyclopenta[b]fluorene (yield: 89.42%).

1. stirringstirred for 12 hours
2. customThe resultant mixture, after removal of solvent
3. dissolutionwas dissolved in ethylacetate
4. washwashed with water three times
5. dry with materialThe organic layer was dried over magnesium sulfate
6. customfollowed by removal of volatile materials
7. customThe dried reaction product
8. custominputted to a 500 mL round flask
9. customwater was completely removed
10. temperatureunder reflux with Dean-Stark
11. customfollowed by separation of the organic layer
12. customThe organic layer collected
13. extractionby extracting the residue with diethyl ether
14. dry with materialwas dried over magnesium sulfate
15. customfollowed by removal of volatile materials
16. custompurified