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

HRID 1464849
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1464849
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]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 866602914-(3-Propylcyclopentyl)cyclohexanecarboaldehyde

Produkt 1

HCID 67992361(4-(3-Propylcyclopentyl)cyclohexyl)methanolAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-19c8f0e582fd4540b00dc927abea3db4
Quelldatensatz
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08999197B2

Notizen zur Reaktion

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