2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21706781、化合物

HRID 1594775ノート

反応式

HRID 1594775 の反応式
Cl[C:2]1[C:3](=[O:14])[C:4]([C:12]#N)=[C:5]([C:10]#N)[C:6](=O)[C:7]=1Cl.[C:15]([O:18][C:19]1C=C2C(=C[C:28]=1[O:29][CH3:30])CCCC2)(=[O:17])[CH3:16]>O1CCOCC1>[C:15]([O:18][C:19]1[CH:12]=[C:4]2[C:5]([CH2:6][CH2:7][CH2:2][C:3]2=[O:14])=[CH:10][C:28]=1[O:29][CH3:30])(=[O:17])[CH3:16]

参加物

4

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 13197843HCID 13197843、化合物

生成物 1

HCID 21706781HCID 21706781、化合物

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
25 °C

実験手順

A solution of 454 mg of 2,3-dichloro-5,6-dicyanobenzoquinone in 4 mL of dioxane was added dropwise over a period of 5 minutes to a stirred solution of 6-acetoxy -7-methoxytetralin in 1 mL of 5% aqueous dioxane at 25° C. under an atmosphere of nitrogen. The resulting solution was stirred at 25° C. for 20 hours. Thereafter the reaction mixture was filtered through a sintered glass funnel and the solid residue of 2,3-dichloro-5,6-dicyaniodihydroquinione was washed with 2 mL of dioxane. The residue wash solution was combined with the filtrate. Thereafter the dioxanie was evaporated from the combined filtrate at reduced atmospheric pressure. The resulting residue was stirred with a mixture of 10 mL of 5% aqueous sodium bicarbonate and 80 mL of ethyl acetate. The ethyl acetate layer was separated and washed successively once with 5 mL of 5% aqueous sodium bicarbonate, once with 5 mL of water, and twice with 5 mL of brine. The ethyl acetate extract was dried over anhydrous magnesium sulfate. The magnesium sulfate was removed by filtration and the ethyl acetate was evaporated from the filtrate at reduced atmospheric pressure. The resulting residue was chromatographed on a column of silica gel eluted by a solution of ethyl acetate and hexane in a ratio of 3 to 5 under a moderate positive pressure to obtain 146 mg of 7-acetoxy-6-methoxytetralin-1-one having m.p. 118.5-119.5° C. MS [M+]234.

後処理

  1. filtrationThereafter the reaction mixture was filtered through a sintered glass funnel
  2. washthe solid residue of 2,3-dichloro-5,6-dicyaniodihydroquinione was washed with 2 mL of dioxane
  3. washThe residue wash solution
  4. customThereafter the dioxanie was evaporated from the combined filtrate at reduced atmospheric pressure
  5. stirringThe resulting residue was stirred with a mixture of 10 mL of 5% aqueous sodium bicarbonate and 80 mL of ethyl acetate
  6. customThe ethyl acetate layer was separated
  7. washwashed successively once with 5 mL of 5% aqueous sodium bicarbonate, once with 5 mL of water
  8. extractionThe ethyl acetate extract
  9. dry with materialwas dried over anhydrous magnesium sulfate
  10. customThe magnesium sulfate was removed by filtration
  11. customthe ethyl acetate was evaporated from the filtrate at reduced atmospheric pressure
  12. customThe resulting residue was chromatographed on a column of silica gel
  13. washeluted by a solution of ethyl acetate and hexane in a ratio of 3 to 5 under a moderate positive pressure

出典と根拠

ORDレコード
ord-05455526604846c7a5cb1b7db6ab26b6
出典データセット
uspto-grants-2001_09
特許番号
US06284789B1

反応ノート

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