Hydrochloric Acid → HCID 54285185, Verbindung

HRID 249554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 249554
C[C:2]1(C)[O:6][CH:5]([CH2:7][C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4](=[O:16])[O:3]1.Cl>C1(C)C=CC=CC=1.C[O-].[Na+]>[OH:6][CH:5]([CH2:7][C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]([O:3][CH3:2])=[O:16]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 19761817HCID 19761817, Verbindung

Produkt 1

HCID 54285185HCID 54285185, VerbindungAusbeute 84,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 10942334Sodium MethoxideLösungsmittel

Versuchsvorschrift

To a solution of ethyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate (480 mg, 1.97 mmol) in toluene (2.0 ml), sodium methoxide (1M in methanol) (2.1 ml) was dropwise added at 0° C. in an argon atmosphere and stirred for 30 minutes. To the mixture, 1N hydrochloric acid (2.1 ml) was dropwise added and the mixture was stirred at room temperature for 15 minutes. After evaporating off the most of the organic solvent under reduced pressure, the mixture was extracted with ethyl acetate and washed with a saturated saline and a phosphate buffer (pH 7.0). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane:ethyl acetate=5:1) to give pure 1-methyl 6-ethyl 2-hydroxy-4-oxoadipate (366 mg, 1.67 mmol). Yield, 85 %.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. customAfter evaporating off the most of the organic solvent under reduced pressure
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with a saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-a3b7dbd6fd97436889d83a527cc76e0e
Quelldatensatz
uspto-grants-1993_05
Patentnummer
US05214197

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