3,5-Dimethylcyclohex-2-en-1-one → 3-Benzyl-3,5-dimethylcyclohexanone

HRID 1292945

Reaktionsgleichung

Reaktionsgleichung von HRID 1292945
[CH2:1]([Mg]Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:10][C:11]1[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH:12]=1>C(OCC)C.Cl[Cu]>[CH2:1]([C:11]1([CH3:10])[CH2:16][CH:15]([CH3:17])[CH2:14][C:13](=[O:18])[CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 142913,5-Dimethylcyclohex-2-en-1-oneHCID 178419663HCID 178419663, Verbindung

Produkt 1

HCID 222215123-Benzyl-3,5-dimethylcyclohexanoneAusbeute 53 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 62652Cuprous chlorideKatalysatorHCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a cooled (−20° C.) 1M benzylmagnesium bromide solution in diethyl ether (50 ml) under argon was added CuCl (0.52 g, 5.3 mmol) and the mixture was stirred for 5 min. Then a solution of 3,5-dimethyl-2-cyclohexen-1-one (12) (4.4 g, 35.1 mmol) in diethyl ether (15 ml) was added dropwise keeping the temperature below −10° C. The mixture was stirred for 2 h and quenched with 10% aqueous acetic acid (40 ml). The organic layer was separated, washed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl, and dried over MgSO4. Filtration and concentration in vacuo afforded oily residue what was separated by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1). Cyclohexanone 13 (4.0 g, 53%) was obtained as a colorless oil.

Aufarbeitung

  1. customthe temperature below −10° C
  2. stirringThe mixture was stirred for 2 h
  3. customquenched with 10% aqueous acetic acid (40 ml)
  4. customThe organic layer was separated
  5. washwashed with water, saturated aqueous NaHCO3 and saturated aqueous NaCl
  6. dry with materialdried over MgSO4
  7. filtrationFiltration and concentration in vacuo
  8. customafforded oily residue what
  9. customwas separated by flash chromatography on silica gel (light petroleum ether-ethyl acetate, 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-c9f41d6b88b5409598f51df05bedfef2
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07238703B2

Verknüpfte Notizen

Wird geladen…