反应详情

Trans-cyclohexane-1,4-diol (4.30 mmol) and sodium hydride (60% suspension in oil, 2.15 mmol) are suspended in dry dimethylsulfoxide (4 mL) and a solution of 4-fluoro-2-trifluoromethyl-benzonitrile (2.15 mmol) in dry dimethylsulfoxide (4 mL) is added dropwise. The resulting mixture is stirred at room temperature. After 1 hour reaction time, the reaction is treated with water (10 mL), the precipitate formed is separated by filtration and the filtrate is extracted with dichloromethane (25 mL). The organic phase is washed with aqueous saturated ammonium chloride (5 mL), dried over magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. The precipitate is triturated with diethylether (15 mL), filtered and the filtrate concentrated under reduced pressure. Both fractions of crude product are combined, dissolved in dichloromethane and purified by chromatography through a short pad of silica gel (dichloromethane and then diethylether as eluents) to afford the desired product (60% yield).

1. customAfter 1 hour reaction time
2. customthe precipitate formed
3. customis separated by filtration
4. extractionthe filtrate is extracted with dichloromethane (25 mL)
5. washThe organic phase is washed with aqueous saturated ammonium chloride (5 mL)
6. dry with materialdried over magnesium sulfate
7. filtrationfiltered
8. concentrationthe filtrate is concentrated under reduced pressure
9. customThe precipitate is triturated with diethylether (15 mL)
10. filtrationfiltered
11. concentrationthe filtrate concentrated under reduced pressure
12. dissolutiondissolved in dichloromethane
13. custompurified by chromatography through a short pad of silica gel (dichloromethane