반응 #1552029

반응 방정식

ammonium chloride

4-(3-propylcyclopentyl)-cyclohexanone

1-bromo-4-ethoxy-2,3-difluorobenzene

n-Butyllithium

→

1-(4-ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol

수율 94.7%

용매

THF

THF

hexane

반응 조건

후처리

1. 1
   온도it was warmed to room temperature
2. 2
   기타The mixture was separated
3. 3
   추출the water layer was extracted with ethyl acetate three times
4. 4
   세척the combined organic layer was washed with brine
5. 5
   건조The solution was dried over anhydrous magnesium sulfate
6. 6
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
7. 7
   기타The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume)

실험 절차

THF (100 ml) was added to 1-bromo-4-ethoxy-2,3-difluorobenzene (5.1 g) in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to −78° C. n-Butyllithium (1.57 M, in a hexane solution) (13.8 ml) was added dropwise at a temperature of −70° C. or lower. The stirring was continued at −78° C. for another 2 hours, and 4-(3-propylcyclopentyl)-cyclohexanone (3.0 g) in a THF (10 ml) solution was added dropwise at a temperature of −70° C. or lower. After the mixture had been stirred at −78° C. for another 1 hour, it was warmed to room temperature, and a saturated aqueous solution of ammonium chloride (50 ml) was added. The mixture was separated, and the water layer was extracted with ethyl acetate three times, and then the combined organic layer was washed with brine. The solution was dried over anhydrous magnesium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/9 by volume) to give 1-(4-ethoxy-2,3-difluorophenyl)-4-(3-propylcyclopentyl)cyclohexanol (5.0 g).

출처