Tetrahydrofuran → 7-[2-[4-(Hydroxymethyl)phenoxy]ethyl]-2,3-dimethoxy-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione

HRID 2268544ノート

反応式

HRID 2268544 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:22]=[CH:21][C:20]([CH2:23][OH:24])=[CH:19][CH:18]=3)[CH2:12][CH2:13][C:7]=2[C:6]([O:25]C)=[C:5]([O:27][CH3:28])[C:4]=1[O:29][CH3:30].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>[OH:24][CH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH2:14][CH:11]2[CH2:12][CH2:13][C:7]3[C:6](=[O:25])[C:5]([O:27][CH3:28])=[C:4]([O:29][CH3:30])[C:3](=[O:2])[C:8]=3[CH2:9][CH2:10]2)=[CH:22][CH:21]=1

参加物

6

反応物 4

HCID 8028TetrahydrofuranHCID 103672,6-Pyridinedicarboxylic acidHCID 180504Ceric ammonium nitrateHCID 183485334-[2-(1,2,3,4-Tetramethoxy-6,7,8,9-tetrahydro-5H-benzo[a]cyclohepten-7-yl)ethoxy]phenylmethanol

生成物 1

HCID 183486057-[2-[4-(Hydroxymethyl)phenoxy]ethyl]-2,3-dimethoxy-4,5,6,7,8,9-hexahydro-1H-benzo[a]cycloheptene-1,4-dione収率 43.8%

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]phenylmethanol (261 mg), 2,6-pyridinedicarboxylic acid (314 mg), THF (6 ml), and water (3 ml) was dropwise added a solution of CAN (1.38 g) in water (3 ml) with cooling with ice. After the reaction mixture was stirred for 15 min, water was added to the reaction mixture, which was then 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=2:1) and then with recrystallization from hexane-ethyl acetate to yield the entitled compound (106 mg) as crystals.

後処理

  1. temperaturewith cooling with ice
  2. extractionwas then 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 The residue
  6. customwas purified by silica gel column chromatography (hexane to hexane:ethyl acetate=2:1)
  7. customwith recrystallization from hexane-ethyl acetate

出典と根拠

ORDレコード
ord-6cdf153bd02c4efbbf8816cbc35bfcc5
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…