Diethyl 2-(ethoxymethylidene)-3-oxobutanedioate → Diethyl 5-ethylpyridine-2,3-dicarboxylate

HRID 864927

Reaktionsgleichung

Reaktionsgleichung von HRID 864927
C(O[CH:4]=[C:5]([C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=O)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.O1CC[N:21]([CH:24]=[CH:25][CH2:26][CH3:27])CC1>C(Cl)Cl>[CH2:26]([C:25]1[CH:4]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:21][CH:24]=1)[CH3:27]

Komponenten

4

Edukt 2

HCID 40590Diethyl 2-(ethoxymethylidene)-3-oxobutanedioateHCID 5809771-Morpholinobutene

Produkt 1

HCID 10857926Diethyl 5-ethylpyridine-2,3-dicarboxylateAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Diethyl ethoxymethyleneoxalacetate (3.17 g, 0.013 mol) is added to a solution of 1-morpholinobutene (1.84 g, 0.013 mol) dissolved in CH2Cl2 (40 mL) at 0°. The solution is concentrated in vacuo, and ammonium acetate (50 g), ammonium hydroxide (10 mL), tetrahydrofuran (20 mL) and 95% ethanol (20 mL) are added. The solution is heated to reflux for 30 minutes, then held at 3° for 72 hours. The reaction solution is then partitioned between water and ethyl acetate. The organic layer is dried over sodium sulfate and concentrated in vacuo to give the product (1.85 g, 0.0074 mol, 57%).

Aufarbeitung

  1. concentrationThe solution is concentrated in vacuo, and ammonium acetate (50 g), ammonium hydroxide (10 mL), tetrahydrofuran (20 mL) and 95% ethanol (20 mL)
  2. additionare added
  3. temperatureThe solution is heated
  4. temperatureto reflux for 30 minutes
  5. customThe reaction solution is then partitioned between water and ethyl acetate
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-44b3eecbd7f6425ca95d17ea9a92ddb1
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05565412

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