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Hydrochloric Acid → 2,6,13,17-Tetramethyloctadecane-9,10-dione

HRID 1176160
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Reaktionsgleichung

Reaktionsgleichung von HRID 1176160
CN1CCN(C)[C:4](=[O:9])[C:3]1=[O:10].[CH3:11][CH:12]([CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH2:13][CH2:14][Li].[CH3:22][CH:23]([CH2:27][CH2:28][CH2:29][CH:30]([CH3:32])[CH3:31])[CH2:24][CH2:25]Br.[Li].Cl>CCOCC>[CH3:31][CH:30]([CH2:29][CH2:28][CH2:27][CH:23]([CH3:22])[CH2:24][CH2:25][C:4](=[O:9])[C:3](=[O:10])[CH2:14][CH2:13][CH:12]([CH3:11])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])[CH3:32]
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Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 1379141-Bromo-3,7-dimethyloctaneHCID 3229831,4-Dimethylpiperazine-2,3-dioneHCID 3028194LithiumHCID 178506868HCID 178506868, Verbindung

Produkt 1

HCID 874415822,6,13,17-Tetramethyloctadecane-9,10-dione

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a suspension of 1,4-dimethylpiperazine-2,3-dione (2.08 g, 1.46×10−2 mol) in 50 ml of dry Et2O was added 3,7-dimethyloctyl lithium (0.45M solution in Et2O, 65 ml, 2.9×10−2 mol, freshly prepared from 3,7-dimethyloctyl bromide and lithium) by a syringe. After 40 min of stirring at room temperature under N2, the solution was hydrolyzed with 100 ml of 10% HCl and extracted with CHCl3. The combined organic layers were washed with saturated aqueous NaHCO3 and dried over Na2SO4. The product was chromatographed on silica gel with 3:1 hexane:CHCl3 as the eluent. Yield=4.446 g (91% based on 65 ml of 0.45M 3,7-dimethyloctyl lithium in Et2O). 1H NMR (250 MHz, CDCl3): δ 2.69-2.78 (m, 4H, —CH2CO), 1.06-1.65 (m, 20H, (CH3)2CHCH2CH2CH2CH(CH3)CH2CH2CO), 0.87 (d, 6H, J=9.0 Hz, —CH3), 0.86 (d, 12H, J=9.5 Hz, —CH3). CI MS m/z: 338.3175 (M+) (calcd 338.318).

Aufarbeitung

  1. extractionextracted with CHCl3
  2. washThe combined organic layers were washed with saturated aqueous NaHCO3
  3. dry with materialdried over Na2SO4
  4. customThe product was chromatographed on silica gel with 3:1 hexane

Quellen und Nachweise

ORD-Eintrag
ord-47f814aca5f941d7bff548479971058c
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07842758B2

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