反应详情

To a solution of sodium hydride (content 60%, 360 mg, 9.00 mmol) in tetrahydrofuran (5 mL) was added dropwise a solution of N-(2-bromophenyl)formamide (1.50 g, 7.50 mmol) in tetrahydrofuran (5 mL) while stirring at room temperature under a nitrogen atmosphere, followed by stirring at the same temperature for 30 minutes. The reaction mixture was cooled to −78° C., n-butyllithium (2.67 M solution in hexane, 3.37 mL, 9.00 mmol) was added dropwise thereto, followed by stirring at the same temperature for 30 minutes. To the reaction mixture was further added dropwise a solution of 3,3,5,5-tetramethylcyclohexanone (771 mg, 5.00 mmol) in tetrahydrofuran (1 mL) at the same temperature, followed by stirring at the same temperature for 1 hour and at room temperature for 1 hour. To the reaction mixture were added water (10 mL), thereafter extraction with ethyl acetate was carried out. The organic layer was washed with water and a 5% aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate, filtrated, and concentrated. To the obtained crude crystals was added ethanol (7.7 mL), followed by heating and stirring at 60° C., and after the crystals were dissolved, the mixture was allowed to cool down to room temperature. Upon confirming the precipitation of crystals, water (6 mL) was added to the mixture, followed by stirring for 2 hours. The crystals were collected by filtration and dried to give 947 mg of the title compound as yellow crystals.

1. stirringby stirring at the same temperature for 30 minutes
2. temperatureThe reaction mixture was cooled to −78° C.
3. stirringby stirring at the same temperature for 30 minutes
4. stirringby stirring at the same temperature for 1 hour and at room temperature for 1 hour
5. extractionextraction with ethyl acetate
6. washThe organic layer was washed with water
7. dry with materiala 5% aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate
8. filtrationfiltrated
9. concentrationconcentrated
10. customTo the obtained crude crystals
11. temperatureby heating
12. stirringstirring at 60° C.
13. dissolutionafter the crystals were dissolved
14. temperatureto cool down to room temperature
15. customthe precipitation of crystals, water (6 mL)
16. additionwas added to the mixture
17. stirringby stirring for 2 hours
18. filtrationThe crystals were collected by filtration
19. customdried