Hexamethylphosphorous triamide → 2-(trans-1-Nonenyl)-3-methyl-4-acetoxy-6-fluoroquinoline

HRID 1613935

Reaktionsgleichung

Reaktionsgleichung von HRID 1613935
C([Li])CCC.[Br-].[CH2:7]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].CN(P(N(C)C)N(C)C)C.[CH:44]([C:46]1[C:55]([CH3:56])=[C:54]([O:57][C:58](=[O:60])[CH3:59])[C:53]2[C:48](=[CH:49][CH:50]=[C:51]([F:61])[CH:52]=2)[N:47]=1)=O>O1CCCC1.O.CCCCCC>[CH:44](/[C:46]1[C:55]([CH3:56])=[C:54]([O:57][C:58](=[O:60])[CH3:59])[C:53]2[C:48](=[CH:49][CH:50]=[C:51]([F:61])[CH:52]=2)[N:47]=1)=[CH:7]\[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Komponenten

8

Edukt 4

HCID 15355Hexamethylphosphorous triamideHCID 3084855Octyltriphenylphosphonium bromideHCID 150070582-Formyl-3-methyl-4-acetoxy-6-fluoroquinolineHCID 178418339Butyllithium

Produkt 1

HCID 150070592-(trans-1-Nonenyl)-3-methyl-4-acetoxy-6-fluoroquinolineAusbeute 10,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

0.29 ml of a hexane solution of 0.48 mmols of n-butyl lithium was added to a solution of 218 mg (0.48 mmols) of octyltriphenylphosphonium bromide in 3 ml of tetrahydrofuran and stirred at room temperature for 5 minutes. This solution was cooled to -78° C., after which 1.43 g (8 mmols) of hexamethylphosphorus triamide was added and stirred for 5 minutes, followed by further addition of 2 ml of a tetrahydrofuran solution of 98.8 mg (0.40 mmols) of 2-formyl-3-methyl-4-acetoxy-6-fluoroquinoline and stirring at -78° C. for 15 minutes and -42° C. for 30 minutes. The reaction solution was added to 20 ml of water and extracted with ethyl acetate, followed by washing with a saturated sodium chloride aqueous solution and drying with anhydrous sodium sulfate. After removal of the solvent by distillation under reduced pressure, the residue was purified by silica gel column chromatography (solvent n-hexane ethyl acetate=30:1 ) to obtain 14 mg (yield 10 %) of 2-(trans-1-nonenyl)-3-methyl-4-acetoxy-6-fluoroquinoline.

Aufarbeitung

  1. temperatureThis solution was cooled to -78° C.
  2. stirringstirred for 5 minutes
  3. stirringstirring at -78° C. for 15 minutes and -42° C. for 30 minutes
  4. extractionextracted with ethyl acetate
  5. washby washing with a saturated sodium chloride aqueous solution
  6. dry with materialdrying with anhydrous sodium sulfate
  7. customAfter removal of the solvent
  8. distillationby distillation under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (solvent n-hexane ethyl acetate=30:1 )

Quellen und Nachweise

ORD-Eintrag
ord-8c551084591e4f9f836d35e9bd028b88
Quelldatensatz
uspto-grants-1993_03
Patentnummer
US05194617

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