Trifluoroacetic acid → 5,6,7,8-Tetrahydro-1,2,3,10,11-pentamethoxydibenzo[a,c]cyclooctene

HRID 1109663노트

반응식

HRID 1109663 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].FC(F)(F)C(O)=O>ClCCl.C(OCC)(=O)C>[CH3:26][O:25][C:17]1[C:16]2[C:6]3[CH:7]=[C:8]([O:9][CH3:10])[C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH2:11][CH2:12][CH2:13][CH2:14][C:15]=2[CH:20]=[C:19]([O:21][CH3:22])[C:18]=1[O:23][CH3:24]

참가 물질

5

반응물 2

HCID 6422Trifluoroacetic acidHCID 151355331-(3,4-Dimethoxyphenyl)-4-(3,4,5-trimethoxyphenyl)butane

생성물 1

HCID 190209825,6,7,8-Tetrahydro-1,2,3,10,11-pentamethoxydibenzo[a,c]cyclooctene수율 24.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

In 1 ml of dichloromethane, 70 mg (0.194 mmol) of 1-(3,4-dimethoxyphenyl)-4-(3,4,5-trimethoxyphenyl)-butane were dissolved. The solution was added with 0.1 ml of trifluoroacetic acid and 180 mg (0.39 mmol) of ferric perchlorate, followed by stirring at room temperature for 40 minutes. The reaction mixture was dissolved in 20 ml of ethyl acetate. The resulting solution was washed with 2N-HCl and then with saturated NaCl. The organic layer was dried over anhydrous magnesium sulfate and the solvent was thereafter distilled off under reduced pressure, whereby brown oil was obtained. The oil thus obtained was purified by thin-film chromatography (silica gel: "MERCK #5744", eluent: 1:5 mixed solvent of ethyl acetate and hexane), whereby 17 mg of the title compound were obtained as colorless oil (yield: 24%). In addition, the starting material was recovered as colorless oil (15 mg, recovery: 21%).

후처리

  1. washThe resulting solution was washed with 2N-HCl
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was thereafter distilled off under reduced pressure, whereby brown oil
  4. customwas obtained
  5. customThe oil thus obtained
  6. customwas purified by thin-film chromatography (silica gel: "MERCK #5744", eluent: 1:5 mixed solvent of ethyl acetate and hexane)

출처 및 근거

ORD 기록
ord-8549f99e341e4500ab458b4c495c12d0
출처 데이터셋
uspto-grants-1994_06
특허 번호
US05321135

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