Ethyl Acetate → Ethyl 4-(2-formylphenylthio)butyrate

HRID 413582

Reaktionsgleichung

Reaktionsgleichung von HRID 413582
F[C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].C(=O)([O-])[O-].[K+].[K+].[SH:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].C(OCC)(=O)C>CN(C)C=O>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[S:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[O:5]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 67970o-FluorobenzaldehydeHCID 271824Ethyl 4-sulfanylbutanoate

Produkt 1

HCID 18533389Ethyl 4-(2-formylphenylthio)butyrateAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, 2-fluorobenzaldehyde (5 g) was dissolved in 15 ml of dimethylformamide and potassium carbonate (8.35 g) was added. Ethyl 4-mercaptobutyrate (8.6 ml) was added at room temperature and was stirred at room temperature for 14 hours. After the addition of 100 ml of ethyl acetate, the mixture was washed with 50 ml of water twice, 50 ml of a 0.5N hydrochloric acid, and 50 ml of water three times. After drying with anhydrous sodium sulfate, the mixture was concentrated. The concentrated matter was subjected to silica gel chromatography (hexane/ethyl acetate=4/1) purification. The resulting effective fractions were concentrated to yield ethyl 4-(2-formylphenylthio)butyrate (6.86 g, Yield 67%).

Aufarbeitung

  1. washthe mixture was washed with 50 ml of water twice
  2. dry with materialAfter drying with anhydrous sodium sulfate
  3. concentrationthe mixture was concentrated
  4. customThe concentrated matter was subjected to silica gel chromatography (hexane/ethyl acetate=4/1) purification
  5. concentrationThe resulting effective fractions were concentrated

Quellen und Nachweise

ORD-Eintrag
ord-be89ac69ae664e8a997bd87039fc1230
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566535B1

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