Hexen-2-al → Diethyl 4-n-propylpyridine-2,3-dicarboxylate

HRID 1936695

Reaktionsgleichung

Reaktionsgleichung von HRID 1936695
Cl[CH:2]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH3:15][C:16](=O)[CH:17]=[CH:18][CH2:19][CH3:20].S(=O)(=O)([O-])[NH2:23].[NH4+]>C(O)C>[CH2:17]([C:18]1[CH:19]=[CH:20][N:23]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[C:2]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:16][CH3:15]

Komponenten

5

Edukt 3

HCID 12990Hexen-2-alHCID 24482Ammonium sulfamateHCID 10998635Diethyl 2-chloro-3-oxobutanedioate

Produkt 1

HCID 22462372Diethyl 4-n-propylpyridine-2,3-dicarboxylateAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of diethyl 3-chloro-2-oxosuccinate (137.4 g, 0.69 mol), hexen-2-al (72.5 g, 0.74 mol) and ammonium sulphamate (190.2 g, 1.66 mol) in ethanol (450 ml) was stirred under reflux for 36 hours and then filtered. The filtrate was evaporated under vacuum, the resulting residue dissolved in water (500 ml) and this solution extracted with ethyl acetate (6×500 ml). The combined organic extracts were dried (MgSO4) and evaporated under vacuum, then the resulting residue was chromatographed on silica gel (50 g), using an ethyl acetate in hexane elution gradient (0-20% ethyl acetate), to give the title compound as an orange oil (34.1 g, 21%). Rf 0.20 (ethyl acetate:hexane, 20:80).

Aufarbeitung

  1. temperatureunder reflux for 36 hours
  2. filtrationfiltered
  3. customThe filtrate was evaporated under vacuum
  4. dissolutionthe resulting residue dissolved in water (500 ml)
  5. extractionthis solution extracted with ethyl acetate (6×500 ml)
  6. dry with materialThe combined organic extracts were dried (MgSO4)
  7. customevaporated under vacuum
  8. customthe resulting residue was chromatographed on silica gel (50 g)
  9. washan ethyl acetate in hexane elution gradient (0-20% ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-cc0872dd258b48ea86be6a68f141cca7
Quelldatensatz
uspto-grants-2002_05
Patentnummer
US06391885B1

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