Réaction #1552031

Équation de réaction

Ethanol

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

sodium borohydride

→

(4-(3-propylcyclopentyl)cyclohexyl)methanol

Rendement 90.5%

Solvants

water

Conditions de réaction

Traitement

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

Mode opératoire

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=1/2 by volume) to give (4-(3-propylcyclopentyl)cyclohexyl)methanol (2.1 g).

Source