Ceric ammonium nitrate → 4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl)benzoic Acid

HRID 1245198ノート

反応式

HRID 1245198 の反応式
C[O:2][C:3]1[C:4]([CH3:31])=[C:5]([C:22]([O:29]C)=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH2:6][C:7]1[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([C:16]2[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=2)[CH:8]=1.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].C(=O)([O-])O.[Na+]>C(#N)C.O>[CH3:26][O:25][C:24]1[C:3](=[O:2])[C:4]([CH3:31])=[C:5]([CH2:6][C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[C:9]([C:16]3[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=3)[CH:8]=2)[C:22](=[O:29])[C:23]=1[O:27][CH3:28]

参加物

6

反応物 3

HCID 180504Ceric ammonium nitrateHCID 516892Sodium BicarbonateHCID 121472804-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl)benzoic acid

生成物 1

HCID 219191784-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-yl)methyl-2-(3-pyridyl)benzoic Acid収率 36%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

4-(3,4,5,6-Tetramethoxy-2-methylbenzyl)-2-(3-pyridyl) benzoic acid (30 mg, 1.1820 mmol) was dissolved in a mixed solvent of acetonitrile (6 ml) and water (2 ml), then CAN (97 mg, 0.1770 mmol) was added thereto at room temperature and the mixture was stirred for 3 hour. The reaction solution was poured into water, neutralized with a saturated aqueous solution of sodium hydrogen carbonate and extracted with ethyl acetate. The extract was washed with water and dried and the solvent was evaporated therefrom. The residue was purified by silica gel column chromatography (10% methanol-methylene chloride) to give the title compound (10 mg, 0.0254 mmol, 36%).

後処理

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was evaporated
  5. customThe residue was purified by silica gel column chromatography (10% methanol-methylene chloride)

出典と根拠

ORDレコード
ord-c2dad807309a42ed857e597d01b43a4d
出典データセット
uspto-grants-2006_10
特許番号
US07122543B2

反応ノート

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