5-Benzyloxyindole → 3-(5-Benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester

HRID 1295143

反応式

HRID 1295143 の反応式
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[CH2:19]([N+](CCCC)(CCCC)CCCC)CCC.[C:36]([O:39][CH2:40][CH3:41])(=[O:38])[CH3:37].[CH3:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]>>[CH2:40]([O:39][C:36](=[O:38])[CH:37]=[C:19]([N:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13]1)[C:44]1[CH:43]=[CH:42][CH:47]=[CH:46][CH:45]=1)[CH3:41]

参加物

4

反応物 3

HCID 146245-BenzyloxyindoleHCID 2724141Tetrabutylammonium FluorideHCID 21226206Ethyl acetate hexane

生成物 1

HCID 674277863-(5-Benzyloxy-indol-1-yl)-3-phenyl-acrylic acid ethyl ester収率 68%

実験手順

A mixture of 5-benzyloxy-1H-indole (4.46 g, 20.0 mmol), phenyl-pripionic acid ethyl ester (7.00 g, 40.0 mmol), and tetrabutylammonium fluoride [1.0 M in THF] (36.0 mL, 50.0 mmol) was stirred for 3 days. After removal of solvent, the crude reaction mixture was submitted to flash chromatography on silica gel with ethyl acetate/hexane (1:4) to give the title compound (5.42 g, 68% yield) as an E/Z isomeric mixture. Mass Spectrum (LCMS, ESI) calculated for C26H24NO3 398.2 (M+H); found 398.2.

後処理

  1. customAfter removal of solvent
  2. customthe crude reaction mixture

出典と根拠

ORDレコード
ord-89def55663cb425aac6e022b938b3054
出典データセット
uspto-grants-2007_07
特許番号
US07241789B2

関連ノート

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