2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 89739681、化合物

HRID 1521800ノート

反応式

HRID 1521800 の反応式
[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH2:9][CH2:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[C:13]([C:17](=[O:19])[CH3:18])[CH:12]=3.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C1(C)C=CC=CC=1>[S:1]1[C:5]([C:6](=[O:8])[CH3:7])=[CH:4][C:3]2[CH:9]=[CH:10][C:11]3[C:16]([C:2]1=2)=[CH:15][CH:14]=[C:13]([C:17](=[O:19])[CH3:18])[CH:12]=3

参加物

4

反応物 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 123269771,1'-(4,5-Dihydronaphtho[1,2-b]thiene-2,7-diyl)di(ethan-1-one)

生成物 1

HCID 89739681HCID 89739681、化合物収率 55%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
110 °C

実験手順

To a stirred solution of 1,1′-(4,5-dihydronaphtho[1,2-b]thiophene-2,7-diyl))diethanone (5c) (1 g, 3.7 mmol) in 30 ml of toluene, DDQ (0.84 g, 3.7 mmol) was added and the mixture was stirred at 110° C. for 60 hr. The reaction mixture was concentrated under reduced pressure, 100 ml water was added and the organics were extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain the crude compound which was purified by column chromatography to obtain 1,1′-(naphtho[1,2-b]thiophene-2,7-diyl)diethanone as a brown solid (10a) (0.45 g, 55%).

後処理

  1. concentrationThe reaction mixture was concentrated under reduced pressure, 100 ml water
  2. additionwas added
  3. extractionthe organics were extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the crude compound which
  7. customwas purified by column chromatography

出典と根拠

ORDレコード
ord-e6f76e7971904a48b97accfc62652a67
出典データセット
uspto-grants-2015_07
特許番号
US09073942B2

反応ノート

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