Cyclohexanone → Spiro(5.5)undecan-1-one

HRID 2070580

Reaktionsgleichung

Reaktionsgleichung von HRID 2070580
CC(C)([O-])C.[K+].[C:7]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.Br[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]Br>C1(C)C=CC=CC=1>[C:7]1(=[O:13])[C:12]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]2)[CH2:11][CH2:10][CH2:9][CH2:8]1

Komponenten

5

Edukt 3

HCID 7967CyclohexanoneHCID 81001,5-DibromopentaneHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 573924Spiro(5.5)undecan-1-oneAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

To a suspension of potassium tert-butoxide (24.4 g) in toluene (100 mL) was added a solution of cyclohexanone (10.67 g) and 1,5-dibromopentane (25 g) in toluene (50 mL) while stirring. The mixture was stirred at 100° C. for 4 hours. After cooling down to room temperature, the resulting solid was filtered and washed with toluene. The filtrate was concentrated and the residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15) to give spiro[5.5]undecan-1-one (11.85 g).

Aufarbeitung

  1. stirringThe mixture was stirred at 100° C. for 4 hours
  2. filtrationthe resulting solid was filtered
  3. washwashed with toluene
  4. concentrationThe filtrate was concentrated
  5. customthe residue was purified by column chromatography on silica gel (ethyl acetate:hexane (volume ratio)=1:15)

Quellen und Nachweise

ORD-Eintrag
ord-8308357151d441059f21afd1306cb7f6
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299296B2

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