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Hydrochloric Acid → 2-(trans-1-Hydroxy-2-nonenyl)-3-methyl-6-fluoro-4-quinolone

HRID 1613941
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1613941
C(=O)([O-])[O-].[K+].[K+].[OH:7][CH:8]([C:17]1[C:26]([CH3:27])=[C:25]([O:28]C(=O)C)[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:32])[CH:23]=2)[N:18]=1)/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].CO.Cl>O>[OH:7][CH:8]([C:17]1[CH:26]([CH3:27])[C:25](=[O:28])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:32])[CH:23]=2)[N:18]=1)/[CH:9]=[CH:10]/[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 11430Potassium CarbonateHCID 150070632-(trans-1-Hydroxy-2-nonenyl)-3-methyl-4-acetoxy-6-fluoroquinoline

Produkt 1

HCID 867466312-(trans-1-Hydroxy-2-nonenyl)-3-methyl-6-fluoro-4-quinoloneAusbeute 72,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel
2×

Versuchsvorschrift

A solution of 715 mg (5.18 mmols) of potassium carbonate in 3 ml of water was added to a solution of 1.86 g (5.18 mmols) of 2-(trans-1-hydroxy-2-nonenyl)-3-methyl-4-acetoxy-6-fluoroquinoline, 50 ml of methanol and 2 ml of water and stirred at room temperature for 10 minutes. After neutralization by addition of 1N hydrochloric acid, the solvent was distilled off under reduced pressure and 30 ml of chloroform was added to the resultant residue, followed by washing with water and drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the resultant residue was purified by silica gel column chromatography (solvent: chloroform : methanol=40:1) to obtain 1.19 g (yield 72 %) of 2-(trans-1-hydroxy-2-nonenyl)-3-methyl-6-fluoro-4-quinolone.

Aufarbeitung

  1. distillationthe solvent was distilled off under reduced pressure and 30 ml of chloroform
  2. additionwas added to the resultant residue
  3. washby washing with water
  4. dry with materialdrying with anhydrous sodium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography (solvent: chloroform : methanol=40:1)

Quellen und Nachweise

ORD-Eintrag
ord-aece128e6fbb414aa508fe8a0386b301
Quelldatensatz
uspto-grants-1993_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05194617

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