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Benzo[a]carbazole → 11-(2-Ethylhexyl)-11H-benzo[a]carbazole

HRID 2203244
ノート
印刷プレビュー

反応式

HRID 2203244 の反応式
[CH:1]1[C:6]2=[C:7]3[C:15](=[CH:16][CH:17]=[C:5]2[CH:4]=[CH:3][CH:2]=1)[C:14]1[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=1)[NH:8]3.[H-].[Na+].Br[CH2:21][CH:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][CH3:26]>CN(C)C=O>[CH2:27]([CH:22]([CH2:23][CH2:24][CH2:25][CH3:26])[CH2:21][N:8]1[C:7]2[C:15](=[CH:16][CH:17]=[C:5]3[CH:4]=[CH:3][CH:2]=[CH:1][C:6]3=2)[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH3:28]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 9196Benzo[a]carbazoleHCID 24758Sodium hydrideHCID 868042-Ethylhexyl bromide

生成物 1

HCID 6713010811-(2-Ethylhexyl)-11H-benzo[a]carbazole収率 101.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To 11H-benzo[a]carbazole (0.70 g; 3.22 mmol) in dimethyl formamide (DMF) (3 mL) is added sodium hydride (0.19 g; 4.67 mmol) at 0° C. After stirring for 1 h at 0° C., 1-bromo-2-ethylhexane (1.24 g; 6.44 mmol) is added at 0° C., and the mixture is stirred at room temperature overnight. The reaction mixture is poured into ice-water, and the crude product is extracted twice with AcOEt (acetic acid ethyl ester). The combined organic layer is washed with H2O and brine, dried over MgSO4, concentrated and dried in vacuo to give a yellow liquid as a crude product (1.08 g). The product is used for the next reaction without further purification. The structure is confirmed by 1H-NMR spectrum (CDCl3). δ [ppm]: 0.80-0.92 (m, 6H), 1.16-1.47 (m, 8H), 2.27 (m, 1H), 4.65-4.69 (m, 2H), 7.27 (td, 1H), 7.44-7.59 (m, 4H), 7.66 (d, 1H), 8.02 (d, 1H), 8.14 (d, 1H), 8.18 (d, 1H), 8.54 (d, 1H).

後処理

  1. stirringthe mixture is stirred at room temperature overnight
  2. extractionthe crude product is extracted twice with AcOEt (acetic acid ethyl ester)
  3. washThe combined organic layer is washed with H2O and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customdried in vacuo

出典と根拠

ORDレコード
ord-712a66078ddd4bb08fe0fa814babb9f9
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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