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

HRID 580877

反応式

HRID 580877 の反応式
[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]

参加物

4

反応物 2

HCID 91229Ethyl 2-oxocyclohexylacetateHCID 102312Benzyloxyamine hydrochloride

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bcb5c37e0f8646e08a9d56e21518df1f
出典データセット
uspto-grants-1999_07
特許番号
US05919790

関連ノート

読み込み中…