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Dimethylformamide → 4-Carbazol-9-ylmethylbenzoic acid methyl ester

HRID 403645
ノート
印刷プレビュー

反応式

HRID 403645 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].CN(C)C=O.[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30]Br)=[CH:26][CH:25]=1>O>[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)=[CH:26][CH:25]=1
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

6

反応物 4

HCID 6228DimethylformamideHCID 6854CarbazoleHCID 24758Sodium hydrideHCID 256687Methyl 4-(bromomethyl)benzoate

生成物 1

HCID 668730724-Carbazol-9-ylmethylbenzoic acid methyl ester収率 20.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

Carbazole (0.80 g, 4.80 mmol) and sodium hydride (NaH) (60% in mineral oil, 0.25 g, 6.2 mmol) were added to a flask, which was charged with argon. DMF (dimethylformamide) (12 mL) was added and the mixture was stirred at 60° C. for 1 hour (h), after which 4-bromomethyl benzoic acid methyl ester (1.16 g, 4.8 mmol) was added, and the mixture was stirred at 80° C. overnight. Water was added and the product was extracted with CH2Cl2 (dichloromethane), dried (Na2SO4, sodium sulfate) and concentrated. The product was purified by column chromatography to give 310 mg of compound 28 as a white solid.

後処理

  1. additionwhich was charged with argon
  2. stirringthe mixture was stirred at 80° C. overnight
  3. extractionthe product was extracted with CH2Cl2 (dichloromethane)
  4. dry with materialdried (Na2SO4, sodium sulfate)
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography

出典と根拠

ORDレコード
ord-c36c2d67a4ed49c8a260d452a962892e
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08748451B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート