Acetone → 1,2,3,4,9,10-Hexahydro-5,8-dimethoxy-2,3-dimethylene-1,4-epoxyanthracene

HRID 444401노트

반응식

HRID 444401 반응식
[CH3:1]I.[CH2:3]=[C:4]1[C:17](=[CH2:18])C2O[CH:5]1[C:6]1[CH2:7][CH:8]3[CH:13]([CH2:14][C:15]=12)[C:12](=[O:20])[CH:11]=[CH:10][C:9]3=O.[C:22](=[O:25])([O-])[O-].[K+].[K+].C[C:29](C)=[O:30]>>[CH3:1][O:20][C:12]1[CH:11]=[CH:10][C:9]([O:30][CH3:29])=[C:8]2[C:13]=1[CH2:14][C:15]1[CH:22]3[O:25][CH:5]([C:6]=1[CH2:7]2)[C:4](=[CH2:3])[C:17]3=[CH2:18]

참가 물질

5

반응물 4

HCID 180AcetoneHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 133409771,2,3,4,8a,9,10,10a-Octahydro-2,3-dimethylene-1,4-epoxyanthracene-5,8-dione

생성물 1

HCID 133409781,2,3,4,9,10-Hexahydro-5,8-dimethoxy-2,3-dimethylene-1,4-epoxyanthracene수율 92%

반응 조건

온도
80 °C

실험 절차

11.21 g (79 mmol) of methyl iodide were added dropwise under nitrogen to a mixture of 2 g (7.9 mmol) of 1,2,3,4,8a,9,10,10a-octahydro-2,3-dimethylene-1,4-epoxy-anthracene-5,8-dione, 10.9 g (79 mmol) of dried potassium carbonate and 100 ml of anhydrous acetone. The mixture was heated to 80° C. for 15 hours, filtered, the filtrate was concentrated, the residue was taken up in 80 ml of chloroform and the solution was washed with three 40 ml portions of water. After drying over magnesium sulphate, concentration and recrystallisation from diethyl ether/tetrahydrofuran/methylene chloride (4:1:2), there were obtained 2.05 g (92%) of 1,2,3,4,9,10-hexahydro-5,8-dimethoxy-2,3-dimethylene-1,4-epoxyanthracene of melting point 177°-178° C. in the form of white crystals.

후처리

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. washthe solution was washed with three 40 ml portions of water
  4. dry with materialAfter drying over magnesium sulphate, concentration and recrystallisation from diethyl ether/tetrahydrofuran/methylene chloride (4:1:2)

출처 및 근거

ORD 기록
ord-3286b27521cc41e8a8cdd4efefffde66
출처 데이터셋
uspto-grants-1981_04
특허 번호
US04264510

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