Реакция #2446071

Уравнение реакции

Ethanol

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

sodium borohydride

→

(4-(3-propylcyclopentyl)cyclohexyl)methanol

Выход 90.5%

Растворители

water

Условия реакции

Обработка

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

Методика

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).

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