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

HRID 444401ノート

反応式

HRID 444401 の反応式
[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]

参加物

5

反応物 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

生成物 1

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

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-3286b27521cc41e8a8cdd4efefffde66
出典データセット
uspto-grants-1981_04
特許番号
US04264510

反応ノート

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