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Methane → HCID 58938610, Verbindung

HRID 598107
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 598107
[C:1]([C:3]1[CH:4]=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:6](=[O:22])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])#[N:2].Cl.[CH4:29].[CH:30](=O)[CH2:31][CH3:32].C(O[BH-](O[C:44](=O)[CH3:45])OC(=O)C)(=O)C.[Na+]>C(O)C.ClCCCl.[OH-].[OH-].[Pd+2]>[CH2:30]([N:2]([CH2:1][C:3]1[CH:4]=[C:5]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:6](=[O:22])[N:7]2[C:12]=1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]1[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=1[CH3:21])[CH2:29][CH2:44][CH3:45])[CH2:31][CH3:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 86613888HCID 86613888, Verbindung

Produkt 1

HCID 58938610HCID 58938610, VerbindungAusbeute 43,8 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 9942167Palladium hydroxideKatalysatorHCID 111,2-DichloroethaneLösungsmittelHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Ethyl 1-cyano-6-mesityl-4-oxo-4H-quinolizine-3-carboxylate (0.110 g, 0.30 mmol) was dissolved in 20 mL ethanol and HCl (0.15 mL) and treated with 20% Pd(OH)2 over charcoal (0.050 g). The solution was evacuated and filled with a hydrogen balloon. After 5 h, the solution was filtered and concentrated to give a yellow solid. The hydrochloride salt was then dissolved in 1,2-dichloroethane (5 mL) and propionaldehyde (0.078 mL, 1.1 mmol) was added followed by sodium triacetoxyborohydride (0.23 g, 1.1 mmol). The reaction was heated to 40° C. overnight. The solution was cooled, quenched with water. Extraction with ethyl acetate was followed by drying the organic layer, concentration, and flash chromatography (ethyl acetate) to give 0.059 g (42% yield) of the title compound.

Aufarbeitung

  1. customThe solution was evacuated
  2. additionfilled with a hydrogen balloon
  3. filtrationthe solution was filtered
  4. concentrationconcentrated
  5. customto give a yellow solid
  6. temperatureThe solution was cooled
  7. customquenched with water
  8. extractionExtraction with ethyl acetate
  9. customby drying
  10. concentrationthe organic layer, concentration, and flash chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-1405864542a34fd3bbac78fbebfdf548
Quelldatensatz
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07897607B2

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