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

HRID 580877

반응식

HRID 580877 반응식
[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]

참가 물질

4

반응물 2

HCID 91229Ethyl 2-oxocyclohexylacetateHCID 102312Benzyloxyamine hydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-bcb5c37e0f8646e08a9d56e21518df1f
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919790

연결된 노트

불러오는 중…