Sodium hydride → HCID 70029796, Verbindung

HRID 413425

Reaktionsgleichung

Reaktionsgleichung von HRID 413425
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][C:10]2=[O:15])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].[CH2:18]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25]CBr)[CH3:19]>CN(C=O)C>[CH2:18]([O:20][C:21](=[O:28])[CH2:22][CH2:23][CH2:24][CH2:25][C:9]1([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:14][CH2:13][CH2:12][CH2:11][C:10]1=[O:15])[CH3:19]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 858682-(3-Methoxyphenyl)cyclohexanoneHCID 117544Ethyl 6-bromohexanoate

Produkt 1

HCID 70029796HCID 70029796, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-(3-Methoxy-phenyl)-cyclohexanone (0.80 g, 4.05 mmol) was added slowly to a suspension of NaH (60%) (0.185 g, 5.1 mmol) in anhydrous DMF (5 mL) at 0° C. under Ar over 15 min. After an additional 15 min. at 20° C. 6-bromohexanoic acid ethyl ester (1.0 g, 4.5 mmol) was added followed by stirring at 60° C. for 6 hr. The reaction mixture was cooled, quenched with saturated NH4Cl solution, partitioned between EtOAc (150 mL) and H2O (100 mL), the organic layer washed with H2O (2×100 mL), dried (Na2SO4), filtered, and concentrated to dryness to give the title compound after silica gel chromatography eluting with hexane:EtOAc, 50:1 to 10:1.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customquenched with saturated NH4Cl solution
  3. custompartitioned between EtOAc (150 mL) and H2O (100 mL)
  4. washthe organic layer washed with H2O (2×100 mL)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-5008655f7c894778974241fa7dbec834
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566385B2

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