反応 #1552031

反応方程式

Ethanol

4-(3-propylcyclopentyl)cyclohexanecarboaldehyde

sodium borohydride

→

(4-(3-propylcyclopentyl)cyclohexyl)methanol

収率 90.5%

溶媒

water

反応条件

後処理

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

実験手順

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).

出典