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Tetrahydrofuran → Ethyl 2-(2,3-dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)acetate

HRID 2268541
ノート
印刷プレビュー

反応式

HRID 2268541 の反応式
C(OCC[CH:7]1[CH2:13][CH2:12][C:11]2[C:14]([O:24]C)=[C:15]([O:22][CH3:23])[C:16]([O:20][CH3:21])=[C:17]([O:18]C)[C:10]=2[CH2:9][CH2:8]1)(=O)C.N1C(C(O)=O)=CC=C[C:27]=1[C:35]([OH:37])=[O:36].[CH2:38]1COC[CH2:39]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+]>O>[CH3:21][O:20][C:16]1[C:17](=[O:18])[C:10]2[CH2:9][CH2:8][CH:7]([CH2:27][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:13][CH2:12][C:11]=2[C:14](=[O:24])[C:15]=1[O:22][CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183485472-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl acetate

生成物 1

HCID 18348562Ethyl 2-(2,3-dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)acetate

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

実験手順

To a mixture of 2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethyl acetate (800 mg), 2,6-pyridinedicarboxylic acid (1.14 g), THF (16 ml), and water (8 ml) was dropwise added a solution of CAN (4.98 g) in water (8 ml) with cooling with ice. After the reaction mixture was stirred for 15 min, water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride and dried. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=4:1) to yield the entitled compound (604 mg) as an oil.

後処理

  1. temperaturewith cooling with ice
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride
  4. customdried
  5. customThe solvent was removed in vacuo
  6. customThe residue was purified by silica gel column chromatography (hexane to hexane:ethyl acetate=4:1)

出典と根拠

ORDレコード
ord-e052533e017e4b2799ba4442d4106386
出典データセット
uspto-grants-2001_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06326369B1

反応ノート

読み込み中…

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