반응 #434482

반응 방정식

cyclohexene oxide

p-tolylbromide

magnesium

→

title compound

수율 52.6%

rac-2-p-Tolyl-cyclohexanone

수율 52.6%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITION(CuBr-dimethylsulfide complex (2.0 g, 10 mmol) was added
2. 2
   온도the reaction warmed to 0° C. at which point
3. 3
   기타an exothermic reaction initiates
4. 4
   온도With ice-bath cooling the temperature
5. 5
   온도can be maintained below 25° C
6. 6
   workup.STIRRINGThe reaction mixture was then stirred at 0–5° C. for an additional 2 h
7. 7
   기타quenched with ammonium chloride solution (saturated, 30 mL)
8. 8
   추출the product extracted with tert-butyl methyl ether
9. 9
   세척The combined organic extracts were then washed with water
10. 10
    건조dried over sodium sulfate
11. 11
    여과filtered
12. 12
    기타evaporated
13. 13
    기타Recrystallisation from hexane

실험 절차

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).

출처