Ethanol → (4-(3-Propylcyclopentyl)cyclohexyl)methanol

HRID 1464849Notes

Reaction equation

C(O)C.[CH2:4]([CH:7]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH:18]=[O:19])[CH2:14][CH2:13]2)[CH2:8]1)[CH2:5][CH3:6].[BH4-].[Na+]>O>[CH2:4]([CH:7]1[CH2:11][CH2:10][CH:9]([CH:12]2[CH2:17][CH2:16][CH:15]([CH2:18][OH:19])[CH2:14][CH2:13]2)[CH2:8]1)[CH2:5][CH3:6]

Participants

Conditions

Temperature: 0 °C

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).

Workup

customobtained in the second step in Example 3, in a reaction vessel under an atmosphere of nitrogen
customhad been returned to room temperature
customThe mixture was separated
extractionthe water layer was extracted with diethyl ether three times
washthe combined organic layer was washed with brine
dry with materialThe solution was dried over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure
customThe residue was purified by silica gel chromatography (eluent: ethyl acetate/n-heptane=1/2 by volume)

Sources & evidence

ORD record: ord-19c8f0e582fd4540b00dc927abea3db4
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08999197B2

Reaction notes

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