반응 #2175432

반응 방정식

ammonia

Lithium aluminum hydride

4-(4′-Hexyloxy-2,3,-difluorophenyl)-cyclohexanone

ethyl acetate

→

trans-4-(4′-hexyloxy-2,3,-difluorophenyl)-cyclohexanol

수율 81.0%

용매

THF

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise to the suspension in the temperature range of −20° C. to −10° C.
2. 2
   온도cooling
3. 3
   기타deposits were removed by filtration through Celite
4. 4
   추출The filtrate was extracted with ethyl acetate
5. 5
   세척The combined organic phase was washed successively with water and brine
6. 6
   건조dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONThe solvent was distilled off under reduced pressure
8. 8
   기타the residue was purified by recrystallization from heptane

실험 절차

Lithium aluminum hydride (1.47 g) was suspended in THF (200 ml). 4-(4′-Hexyloxy-2,3,-difluorophenyl)-cyclohexanone (s-14) (20.0 g) dissolved in THF (50 ml) was added dropwise to the suspension in the temperature range of −20° C. to −10° C., and the stirring was continued in this temperature range for another 2 hours. After the completion of the reaction had been confirmed by means of GC analysis, ethyl acetate and then a saturated aqueous solution of ammonia were added to the reaction mixture under ice-cooling and deposits were removed by filtration through Celite. The filtrate was extracted with ethyl acetate. The combined organic phase was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by recrystallization from heptane to give trans-4-(4′-hexyloxy-2,3,-difluorophenyl)-cyclohexanol (s-29) (16.3 g). The yield based on the compound (s-27) was 81.0%.

출처