Tert-Butyl nitrite → 2-(Hydroxyimino)-2-phenyl-1-p-tolylethanone

HRID 1430594노트

반응식

HRID 1430594 반응식
[C:1]1([CH2:7][C:8]([C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:17](OC(C)(C)C)=[O:18].[O-]CC.[Na+]>CCO>[OH:18][N:17]=[C:7]([C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[C:8]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)=[O:9]

참가 물질

5

반응물 3

HCID 10906Tert-Butyl nitriteHCID 2280161-(4-Methylphenyl)-2-phenylethan-1-oneHCID 2723922Sodium ethoxide

생성물 1

HCID 866581402-(Hydroxyimino)-2-phenyl-1-p-tolylethanone수율 93.3%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-phenyl-1-p-tolylethanone (5.0 g, 23.78 mmol) in EtOH (475.0 mL) at room temperature was added dropwise tert-butyl nitrite (5.5 mL, 46.2 mmol) followed by sodium ethoxide (4.07 g, 59.8 mmol). The reaction was stirred at room temperature overnight and concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with H2O, brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography to give the title compound as an orange oil (5.31 g). LCMS m/z=239.9 [M+H]+.

후처리

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with H2O, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-81312b9822384ab5b5a605dca10facff
출처 데이터셋
uspto-grants-2015_01
특허 번호
US08940891B2

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