Tetrahydrofuran → 4-[2-(2,3-Dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid

HRID 2268545ノート

反応式

HRID 2268545 の反応式
C[O:2][C:3]1[C:8]2[CH2:9][CH2:10][CH:11]([CH2:14][CH2:15][O:16][C:17]3[CH:25]=[CH:24][C:20]([C:21]([OH:23])=[O:22])=[CH:19][CH:18]=3)[CH2:12][CH2:13][C:7]=2[C:6]([O:26]C)=[C:5]([O:28][CH3:29])[C:4]=1[O:30][CH3:31].N1C(C(O)=O)=CC=CC=1C(O)=O.C1COCC1.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>[CH3:29][O:28][C:5]1[C:6](=[O:26])[C:7]2[CH2:13][CH2:12][CH:11]([CH2:14][CH2:15][O:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:24][CH:25]=3)[CH2:10][CH2:9][C:8]=2[C:3](=[O:2])[C:4]=1[O:30][CH3:31]

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183486524-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid

生成物 1

HCID 183485244-[2-(2,3-Dimethoxy-1,4-dioxo-4,5,6,7,8,9-hexahydro-1H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid収率 43%

試薬・触媒・溶媒 1

HCID 962Water溶媒3 回

実験手順

To a mixture of 4-[2-(1,2,3,4-tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]benzoic acid (1.00 g), 2,6-pyridinedicarboxylic acid (1.16 g), THF (40 ml), and water (10 ml) was dropwise added a solution of CAN (5.09 g) in water (10 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 combined solvent of ethyl acetate and THF. The organic layer was washed with water, and saturated aqueous sodium chloride, and dried. The solvent was removed in vacuo. The residue was recrystallized from THF-ethyl acetate to yield the entitled compound (400 mg) as crystals.

後処理

  1. temperaturewith cooling with ice
  2. extractionwas extracted with combined solvent of ethyl acetate and THF
  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 recrystallized from THF-ethyl acetate

出典と根拠

ORDレコード
ord-7270509900a14d539a76243c81853ee8
出典データセット
uspto-grants-2001_12
特許番号
US06326369B1

反応ノート

読み込み中…