Ethyl 2-oxocyclohexylacetate → (2-Benzyloxyimino-cyclohexyl)-acetic acid ethyl ester

HRID 580877

Reaktionsgleichung

Reaktionsgleichung von HRID 580877
[CH3:1][CH2:2][O:3][C:4]([CH2:6][CH:7]1[C:12](=O)[CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:5].Cl.[CH2:15]([O:22][NH2:23])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(O)C>[CH2:2]([O:3][C:4](=[O:5])[CH2:6][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][C:12]1=[N:23][O:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[CH3:1]

Komponenten

4

Edukt 2

HCID 91229Ethyl 2-oxocyclohexylacetateHCID 102312Benzyloxyamine hydrochloride

Produkt 1

HCID 54396605(2-Benzyloxyimino-cyclohexyl)-acetic acid ethyl esterAusbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Ethyl 2-cyclohexanoneacetate (4.28 g, 23.3 mmol) and O-benzyl hydroxylamine hydrochloride were combined in 100 mL of ethanol (EtOH) and 2.59 g (25.6 mmol, 3.55 mL) of triethyl amine(Et3N) was added. The reaction was stirred at room temperature for 12 hours at which point it was concentrated in vacuo. The residue was taken up in EtOAc and washed with 1N HCl (2×20 mL), saturated NaHCO3 (1×20 mL), dried over Na2SO4, filtered, and concentrated. Purification by chromatography (SiO2, 90:1 hexanes-EtOAc) afforded (2-benzyloxyimino-cyclohexyl)-acetic acid ethyl ester (4.76 g, 72%) as a mixture of oxime isomers.

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. washwashed with 1N HCl (2×20 mL), saturated NaHCO3 (1×20 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by chromatography (SiO2, 90:1 hexanes-EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-bcb5c37e0f8646e08a9d56e21518df1f
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05919790

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