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Adipoyl chloride → 1,6-bis-[11-(2-ethylhexyl)-5-(2,4,6-trimethyl-benzoyl)-11H-benzo[a]-carbazol-8-yl]-hexane-1,6-dione

HRID 2203250
ノート
印刷プレビュー

反応式

HRID 2203250 の反応式
[CH2:1]([CH:3]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH3:2].[CH3:26][C:27]1[CH:35]=[C:34]([CH3:36])[CH:33]=[C:32]([CH3:37])[C:28]=1[C:29](Cl)=[O:30].[Al+3].[Cl-].[Cl-].[Cl-].[C:42](Cl)(=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][C:47](Cl)=[O:48]>C(Cl)Cl>[CH2:1]([CH:3]([CH2:22][CH2:23][CH2:24][CH3:25])[CH2:4][N:5]1[C:17]2[C:12](=[CH:13][C:14]([C:29](=[O:30])[C:28]3[C:27]([CH3:26])=[CH:35][C:34]([CH3:36])=[CH:33][C:32]=3[CH3:37])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=2)[C:11]2[C:6]1=[CH:7][CH:8]=[C:9]([C:42](=[O:50])[CH2:43][CH2:44][CH2:45][CH2:46][C:47]([C:9]1[CH:10]=[C:11]3[C:6](=[CH:7][CH:8]=1)[N:5]([CH2:4][CH:3]([CH2:1][CH3:2])[CH2:22][CH2:23][CH2:24][CH3:25])[C:17]1[C:12]3=[CH:13][C:14]([C:29](=[O:30])[C:28]3[C:32]([CH3:37])=[CH:33][C:34]([CH3:36])=[CH:35][C:27]=3[CH3:26])=[C:15]3[CH:21]=[CH:20][CH:19]=[CH:18][C:16]3=1)=[O:48])[CH:10]=2)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 61034Adipoyl chlorideHCID 970382,4,6-Trimethylbenzoyl chlorideHCID 6451240Aluminum(III) Chloride2 回HCID 6713010811-(2-Ethylhexyl)-11H-benzo[a]carbazole

生成物 1

HCID 896280231,6-bis-[11-(2-ethylhexyl)-5-(2,4,6-trimethyl-benzoyl)-11H-benzo[a]-carbazol-8-yl]-hexane-1,6-dione

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To 11-(2-ethylhexyl)-11H-benzo[a]carbazole (1.65 g; 5.00 mmol) in CH2Cl2 (15 mL) are added 2,4,6-trimethylbenzoyl chloride (0.92 g; 5.11 mmol) and AlCl3 (0.70 g; 5.25 mmol) at 0° C. After stirring at room temperature for 1 hour, AlCl3 (0.70 g; 5.30 mmol) is added at 0° C. and adipoyl chloride (0.43 g; 2.33 mmol) is added dropwise, and then the mixture is stirred at room temperature overnight. The reaction mixture is poured into ice-water, and the crude product is extracted twice with CH2Cl2. The combined organic layer is washed with water and brine, dried over MgSO4, and concentrated to give a green solid. The crude product is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:1) to give a beige solid (0.85 g; 34.4%). The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.82 (t, 6H), 0.89 (t, 6H), 1.17-1.42 (m, 16H), 1.93 (br, 4H), 2.21 (s, 12H), 2.26 (m, 2H), 2.40 (s, 6H), 3.18 (br, 4H), 4.69 (m, 4H), 6.97 (s, 4H), 7.54 (d, 2H), 7.69-7.78 (m, 4H), 8.08 (s, 2H), 8.39 (s, 2H), 8.61 (br, 4H), 9.53 (d, 2H).

後処理

  1. stirringthe mixture is stirred at room temperature overnight
  2. extractionthe crude product is extracted twice with CH2Cl2
  3. washThe combined organic layer is washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customto give a green solid
  7. customThe crude product is purified by column chromatography on silica gel eluting with a mixed solvent of CH2Cl2 and n-hexane (1:1)
  8. customto give a beige solid (0.85 g; 34.4%)

出典と根拠

ORDレコード
ord-17f2dcde0f5b4661aefdb693a757e1a8
出典データセット
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09365515B2

反応ノート

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