反应详情

温度

-78 °C

In an argon gas stream and at −78° C., n-butyl lithium (a 1.57M hexane solution, 0.701 ml, 1.10 mmol) was added to a dimethoxyethane (5 ml) solution of the 2-[(4-chlorophenyl)sulfonylmethyl]-1,4-difluorobenzene (303 mg, 1.00 mmol) obtained in Example 5. The mixture was stirred at −78° C. for 1 hour and then, at room temperature for 30 minutes. The reaction mixture was cooled to −78° C., followed by the dropwise addition of 4-(t-butyldimethylsilyloxy)-1-iodobutane (0.260 ml, 1.00 mmol). While elevating the temperature of the reaction mixture to room temperature, stirring was conducted for 15 hours. Water was added to the reaction mixture, followed by extraction with diethyl ether. The extracts were combined, washed successively with water and brine, dried over MgSO4, and concentrated. The residue thus obtained was purified by medium-pressure chromatography on a silica gel column (8% ethyl acetate-hexane), whereby the title compound (401 mg, 82%) was obtained as a colorless solid. The resulting solid was recrystallized from hexane to yield colorless needle crystals.

1. waitat room temperature for 30 minutes
2. temperatureThe reaction mixture was cooled to −78° C.
3. customto room temperature
4. stirringstirring
5. waitwas conducted for 15 hours
6. extractionfollowed by extraction with diethyl ether
7. washwashed successively with water and brine
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customThe residue thus obtained
11. customwas purified by medium-pressure chromatography on a silica gel column (8% ethyl acetate-hexane), whereby the title compound (401 mg, 82%)
12. customwas obtained as a colorless solid
13. customThe resulting solid was recrystallized from hexane
14. customto yield colorless needle crystals