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

HRID 24004

반응식

HRID 24004 반응식
[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.C(OC(=O)[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH3:23])C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:49]([O:52][CH2:53][CH3:54])(=[O:51])C.CCCCCC>>[CH2:53]([O:52][C:49](=[O:51])[CH:23]=[C:22]([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:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[CH3:54]

참가 물질

5

반응물 4

HCID 146245-BenzyloxyindoleHCID 99643Benzeneacetic acid, alpha-methyl-, ethyl esterHCID 2724141Tetrabutylammonium FluorideHCID 21226206Ethyl acetate hexane

생성물 1

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

실험 절차

A mixture of 5-benzyloxy-1H-indole (4.46 g, 20.0 mmol), phenyl-propionic 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.

후처리

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

출처 및 근거

ORD 기록
ord-4efd4aef04b54ee0bfbdd869d97960bb
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855722B2

연결된 노트

불러오는 중…