Diethyl Ether → 5,9-Diethyltridecan-7-one

HRID 2193827Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2193827
[CH2:1]([CH:3]([CH2:7][CH2:8][CH2:9][CH3:10])[CH2:4][Mg]Br)[CH3:2].[CH2:11]([CH:13]([CH2:17][CH2:18][CH2:19][CH3:20])CC#N)[CH3:12].C([O:23][CH2:24][CH3:25])C>>[CH2:1]([CH:3]([CH2:4][C:24](=[O:23])[CH2:25][CH:13]([CH2:11][CH3:12])[CH2:17][CH2:18][CH2:19][CH3:20])[CH2:7][CH2:8][CH2:9][CH3:10])[CH3:2]

Komponenten

4

Edukt 3

HCID 3283Diethyl Ether2×HCID 1376483-EthylheptanenitrileHCID 178443576HCID 178443576, Verbindung

Produkt 1

HCID 52133715,9-Diethyltridecan-7-one

Versuchsvorschrift

A Grignard solution of 2-ethylhexylmagnesiumbromide in diethylether (1.0 M, 47 mL, 47 mmol) was slowly added via syringe to a stirred mixture of 3-ethylheptanenitrile (VI) (3.3 g, 24 mmol) in diethyl ether (50 mL) at 0° C. under N2 atmosphere. After stirring for 12 h at reflux temperature, the reaction was quenched with an aqueous HCl-solution (2.0 M, 50 mL) at 0° C. and subsequently vigorously stirred for an additional 3 h at room temperature. The organic phase was separated and the aqueous phase was extracted with diethylether. The combined organic phases were washed with a saturated bicarbonate solution and brine, dried over MgSO4 and evaporated under reduced pressure to give a crude brown oil. The resulting brown oil was purified by vacuum distillation (95° C., 10−2 mbar) to afford a yellow oil (VII). (5.8 g, 35%). 1H-NMR (CDCl3): δ=2.66-2.63 (m, 2H), 2.24 (d, J=6.9 Hz, 4H), 1.36-1.04 (m, 16H), 0.91-0.63 (m, 12H). 13C-NMR (CDCl3): δ=211.59, 48.32, 39.74, 35.53, 33.57, 30.22, 26.65, 23.59, 14.61.

Aufarbeitung

  1. temperatureat reflux temperature
  2. customthe reaction was quenched with an aqueous HCl-solution (2.0 M, 50 mL) at 0° C.
  3. stirringsubsequently vigorously stirred for an additional 3 h at room temperature
  4. customThe organic phase was separated
  5. extractionthe aqueous phase was extracted with diethylether
  6. washThe combined organic phases were washed with a saturated bicarbonate solution and brine
  7. dry with materialdried over MgSO4
  8. customevaporated under reduced pressure
  9. customto give a crude brown oil
  10. distillationThe resulting brown oil was purified by vacuum distillation (95° C., 10−2 mbar)

Quellen und Nachweise

ORD-Eintrag
ord-2bd5dedf247b4ea281d1c48ea167b051
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329923B2

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