HCID 22734448, Verbindung → HCID 22734278, Verbindung

HRID 1057906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1057906
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][CH:9]([C:11]1[C:20]2[O:19][CH2:18][CH2:17][O:16][C:15]=2[C:14]([O:21][CH3:22])=[CH:13][CH:12]=1)[OH:10].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:23])[C:7]=1[CH2:8][C:9]([C:11]1[C:20]2[O:19][CH2:18][CH2:17][O:16][C:15]=2[C:14]([O:21][CH3:22])=[CH:13][CH:12]=1)=[O:10]

Komponenten

4

Edukt 2

HCID 22734448HCID 22734448, VerbindungHCID 131709961Jones' reagent

Produkt 1

HCID 22734278HCID 22734278, VerbindungAusbeute 100,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Versuchsvorschrift

Compound 178a (3.0 g) obtained in Step A was dissolved in acetone (30 ml), mixed with Jones reagent (2.6 M) (4.9 ml), and stirred at room temperature for 2 hours. The reaction solution was concentrated under reduced pressure. The resulting residue was mixed with water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried over magnesium sulfate anhydride, and evaporated under reduced pressure for removing the solvent. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1) to give Compound 178(3.0 g, 75%) as colorless crystals.

Aufarbeitung

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionThe resulting residue was mixed with water
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate anhydride
  6. customevaporated under reduced pressure
  7. customfor removing the solvent
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=4/1)

Quellen und Nachweise

ORD-Eintrag
ord-a660f2639d67473f9f20935b879af2b9
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06514996B2

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