Reaction #1552031

Reaction equation

Ethanol

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

sodium borohydride

→

(4-(3-propylcyclopentyl)cyclohexyl)methanol

Yield 90.5%

Solvents

water

Conditions

Workup

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

Procedure

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