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 2268544노트

반응식

HRID 2268544 반응식
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

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매3회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6cdf153bd02c4efbbf8816cbc35bfcc5
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326369B1

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