Reaktion #2446071

Reaktionsgleichung

Ethanol

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

sodium borohydride

→

(4-(3-propylcyclopentyl)cyclohexyl)methanol

Ausbeute 90.5%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle