反应详情

温度

-20 °C

To a solution of p-tolylbromide (17.1 g, 100 mmol) in dry THF (100 mL) was added magnesium (2.43 g, 100 mmol) and then the resulting mixture was cooled to −20° C. and (CuBr-dimethylsulfide complex (2.0 g, 10 mmol) was added and the mixture stirred at −20° C. for 10 min. Then a solution of cyclohexene oxide (10 mL, 100 mmol) in dry THF (10 mL) was added dropwise and the reaction warmed to 0° C. at which point an exothermic reaction initiates. With ice-bath cooling the temperature can be maintained below 25° C. The reaction mixture was then stirred at 0–5° C. for an additional 2 h, then quenched with ammonium chloride solution (saturated, 30 mL) and the product extracted with tert-butyl methyl ether. The combined organic extracts were then washed with water, dried over sodium sulfate, filtered and evaporated. Recrystallisation from hexane afforded the title compound (9.9 g, 52%) as white crystals. MS: m/e=190.1 (M).

1. addition(CuBr-dimethylsulfide complex (2.0 g, 10 mmol) was added
2. temperaturethe reaction warmed to 0° C. at which point
3. customan exothermic reaction initiates
4. temperatureWith ice-bath cooling the temperature
5. temperaturecan be maintained below 25° C
6. stirringThe reaction mixture was then stirred at 0–5° C. for an additional 2 h
7. customquenched with ammonium chloride solution (saturated, 30 mL)
8. extractionthe product extracted with tert-butyl methyl ether
9. washThe combined organic extracts were then washed with water
10. dry with materialdried over sodium sulfate
11. filtrationfiltered
12. customevaporated
13. customRecrystallisation from hexane