Triethylamine → Ethyl(3s)-3-(acetoacetyloxy)butanoate

HRID 639140Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 639140
[OH:1][C@@H:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH2:10](N(CC)CC)C.[CH2:17]=[C:18]1[O:22][C:20](=[O:21])C1>C1(C)C=CC=CC=1>[C:4]([O:6][C@@H:7]([CH3:10])[CH2:8][C:20]([O:22][CH2:18][CH3:17])=[O:21])(=[O:5])[CH2:3][C:2]([CH3:9])=[O:1]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 12661DiketeneHCID 6950306Butanoic acid, 3-hydroxy-, ethyl ester, (3S)-

Produkt 1

HCID 58922490Ethyl(3s)-3-(acetoacetyloxy)butanoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

5.7 g (43.2 mmol) Ethyl(3S)-3-hydroxybutanoate and 44 mg (0.43 mmol) triethylamine are dissolved in 40 ml toluene. At 90° C., 4.7 g (56.1 mmol) diketene are added dropwise. The reaction mixture is stirred at 100° C. for one hour. After cooling down to room temperature, the mixture is poured into ice-water. The phases are separated and the aqueous phase is extracted two times with toluene. The combined organic phases are dried over sodium sulfate, the solvent is removed in vacuo and the residue is purified by column chromatography on silica with cyclohexane/ethyl acetate mixtures as eluent.

Aufarbeitung

  1. temperatureAfter cooling down to room temperature
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted two times with toluene
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customthe residue is purified by column chromatography on silica with cyclohexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-cdd56ef47bf249b08d5a38b85c1bfffc
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07691854B2

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