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Toluene → methyl 2-[2-methyl-1-(4-nitrobenzyl)-1H-indol-3-yl]acetate

HRID 589332
ノート
印刷プレビュー

反応式

HRID 589332 の反応式
C1(C)C=CC=CC=1.[CH3:8][C:9]1[NH:10][C:11]2[C:16]([C:17]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=[CH:13][CH:12]=2.[N+:23]([C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1)([O-:25])=[O:24].C(=O)([O-])[O-].[Cs+].[Cs+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.O>[CH3:8][C:9]1[N:10]([CH2:30][C:29]2[CH:32]=[CH:33][C:26]([N+:23]([O-:25])=[O:24])=[CH:27][CH:28]=2)[C:11]2[C:16]([C:17]=1[CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=[CH:13][CH:12]=2
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 1140TolueneHCID 10796Cesium carbonateHCID 660114-Nitrobenzyl bromideHCID 10774509Sbb044946

生成物 1

HCID 89590250methyl 2-[2-methyl-1-(4-nitrobenzyl)-1H-indol-3-yl]acetate収率 3.7%

試薬・触媒・溶媒 2

HCID 84716
Hexadecyltributylphosphonium bromide
触媒
HCID 962Water溶媒

実験手順

Into 100 mL toluene were added methyl 2-(2-methyl-1H-indol-3-yl)acetate (4.9 g, 24.1 mmol), p-nitro benzyl bromide (5.18 g, 24.0 mmol), cesium carbonate (9.38 g, 28.8 mmol), and cetyl tributyl phosphonium bromide (1.58 g, 3.1 mmol). Upon completion of addition, it was reacted at 110° C. for 6 hours. Upon completion of the reaction, it was cooled, water was added, and extracted with diethyl ether. The extract was washed with water. The organic phase was rotate evaporated to dryness, and purified by preparative liquid phase to obtain the product 300 mg, at a yield of 3.7%.

後処理

  1. additionUpon completion of addition, it
  2. customwas reacted at 110° C. for 6 hours
  3. customUpon completion of the reaction, it
  4. temperaturewas cooled
  5. extractionextracted with diethyl ether
  6. washThe extract was washed with water
  7. customThe organic phase was rotate evaporated to dryness
  8. custompurified by preparative liquid phase

出典と根拠

ORDレコード
ord-6b0a7c77c1b04060bd0ac9cdcaf89dd8
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09233098B2

反応ノート

読み込み中…

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