반응 #2446071

반응 방정식

Ethanol

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

sodium borohydride

→

(4-(3-propylcyclopentyl)cyclohexyl)methanol

수율 90.5%

용매

water

반응 조건

후처리

1. 1
   기타obtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen
2. 2
   기타had been returned to room temperature
3. 3
   기타The mixture was separated
4. 4
   추출the water layer was extracted with diethyl ether three times
5. 5
   세척the combined organic layer was washed with brine
6. 6
   건조The solution was dried over anhydrous magnesium sulfate
7. 7
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
8. 8
   기타The residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=½ by volume)

실험 절차

Ethanol (30 ml) was added to 4-(3-propylcyclopentyl)cyclohexanecarboaldehyde (2.3 g) obtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen, and the mixture was cooled to 0° C., and sodium borohydride (0.22 g) was added slowly. After the mixture had been returned to room temperature and stirred for another 20 hours and water (30 ml) was added. The mixture was separated, and the water layer was extracted with diethyl ether 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=½ by volume) to give (4-(3-propylcyclopentyl)cyclohexyl)methanol (2.1 g).

출처