Ceric ammonium nitrate → 3-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]acrylic acid

HRID 496333ノート

反応式

HRID 496333 の反応式
C[O:2][C:3]1[C:20]([O:21][CH3:22])=[C:19]([O:23][CH3:24])[C:18]([O:25]C)=[C:17]([CH3:27])[C:4]=1[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=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(#N)C.O>[CH3:24][O:23][C:19]1[C:18](=[O:25])[C:17]([CH3:27])=[C:4]([CH2:5][C:6]2[CH:11]=[CH:10][C:9]([CH:12]=[CH:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=2)[C:3](=[O:2])[C:20]=1[O:21][CH3:22]

参加物

5

反応物 2

HCID 180504Ceric ammonium nitrateHCID 73183726HCID 73183726、化合物

生成物 1

HCID 695470173-[4-(5,6-Dimethoxy-3-methyl-1,4-benzoquinon-2-ylmethyl)phenyl]acrylic acid収率 84%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒

実験手順

The compound (589 mg, 1.58 mmol) obtained in Step 1 was dissolved in a mixture of acetonitrile (30 ml) and water (10 ml), to which was added CAN (1.38 g, 2.52 mmol) and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and was extracted with ether. After the extract was washed with water and dried, the solvent was distilled off. The residue was purified by a silica gel column chromatography (5% methanol-methylene chloride) to yield the title compound (452 mg, 1.32 mmol, yield 84%).

後処理

  1. extractionwas extracted with ether
  2. washAfter the extract was washed with water
  3. customdried
  4. distillationthe solvent was distilled off
  5. customThe residue was purified by a silica gel column chromatography (5% methanol-methylene chloride)

出典と根拠

ORDレコード
ord-efd6c23a077b4196a199cb036686d72a
出典データセット
uspto-grants-2005_09
特許番号
US06943196B1

反応ノート

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