Hydrochloric Acid → Diethyl 4-acetoxy-4-phenyl-1,3-butanedicarboxylate

HRID 263692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 263692
CN(C1C=CC=CN=1)C.[OH:10][CH:11]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:12]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[C:31](OC(=O)C)(=[O:33])[CH3:32].Cl>N1C=CC=CC=1>[C:31]([O:10][CH:11]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH:12]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])(=[O:33])[CH3:32]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 19038618Diethyl 4-hydroxy-4-phenyl-1,3-butanedicarboxylate

Produkt 1

HCID 19038620Diethyl 4-acetoxy-4-phenyl-1,3-butanedicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

5 mg of dimethylaminopyridine was added to a mixed solution comprising 500 mg of diethyl 4-hydroxy-4-phenyl-1,3-butanedicarboxylate, 5 ml of pyridine and 1 ml of acetic anhydride, followed by stirring at room temperature overnight. 2N hydrochloric acid was added to the reaction solution, and then the mixture was extracted with ethyl acetate. The organic layer was washed sequentially with 2N hydrochloric acid, a saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain 497 mg of the above-identified compound as colorless oily substance.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed sequentially with 2N hydrochloric acid
  3. dry with materiala saturated sodium hydrogencarbonate aqueous solution and a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate
  4. filtrationThe drying agent was filtered off
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-2f2715a4788d454dab2ffe49e3f9b3d4
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05643958

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