Acetyl chloride → HCID 178471607, Verbindung

HRID 654999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 654999
[CH2:1]([O:3][C:4]([CH:6]([CH3:14])[C:7](=O)[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[O:5])[CH3:2].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:23](Cl)(=[O:25])[CH3:24]>CO>[C:23]([C:8](=[C:7]([NH:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH:6]([CH3:14])[C:4]([O:3][CH2:1][CH3:2])=[O:5])[C:9]([O:11][CH3:12])=[O:10])(=[O:25])[CH3:24]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 7504BenzylamineHCID 14348549Methyl 4-ethoxycarbonyl-3-oxopentanoate

Produkt 1

HCID 178471607HCID 178471607, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

Methyl 4-ethoxycarbonyl-3-oxopentanoate (200 ml; 1.06 mmole) was dissolved in dry methanol (2.5 ml), and benzylamine (386 mg; 3.6 mmole) and molecular sieve 3A (0.3 g) were added thereto. A solution of acetyl chloride (170 mg; 2.17 mmole) in dry methanol (0.9 ml) was added to the resultant mixture, followed by allowing to stand at room temperature for 16 hours. Molecular sieve was removed by filtraton, and the filtrate was diluted with ethyl acetate, washed successively with a saturated sodium bicarbonate solution and water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was dissolved in toluene (2.5 ml). Gaseous ketene was introduced therein at room temperature. After completion of the reaction, the solvent was removed under reduced pressure, and the residue was purified by silica gel column chromatography to give methyl ethyl 2-acetyl-3-benzylamino-4-methyl-2-pentenedioate.

Aufarbeitung

  1. customMolecular sieve was removed by filtraton
  2. additionthe filtrate was diluted with ethyl acetate
  3. washwashed successively with a saturated sodium bicarbonate solution and water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. dissolutionThe residue was dissolved in toluene (2.5 ml)
  7. additionGaseous ketene was introduced
  8. customat room temperature
  9. customAfter completion of the reaction
  10. customthe solvent was removed under reduced pressure
  11. customthe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-faf2c9fc1d9a4143b6d40e546cdac883
Quelldatensatz
uspto-grants-1992_07
Patentnummer
US05134231

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