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

HRID 1430594ノート

反応式

HRID 1430594 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-81312b9822384ab5b5a605dca10facff
出典データセット
uspto-grants-2015_01
特許番号
US08940891B2

反応ノート

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