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3',4',5'-Trimethoxyacetophenone → (E)-3-(6-Methoxyindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one

HRID 618114
Notes
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Reaction equation

HRID 618114 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:16][O:17][C:18]1[CH:26]=[C:25]2[C:21]([C:22]([CH:27]=O)=[CH:23][NH:24]2)=[CH:20][CH:19]=1>>[CH3:16][O:17][C:18]1[CH:26]=[C:25]2[C:21]([C:22](/[CH:27]=[CH:14]/[C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:15])=[CH:23][NH:24]2)=[CH:20][CH:19]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 2

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 9072146-Methoxy-1H-indole-3-carboxaldehyde

Product 1

HCID 21850283(E)-3-(6-Methoxyindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-oneYield 32%

Procedure

Substantially the same procedure as in Example 1 was repeated using 3',4',5'-trimethoxyacetophenone (659 mg) and 6-methoxyindole-3-carboxaldehyde (550 mg) except that the reaction solution was concentrated under reduced pressure, that the residue was purified by silica gel column chromatography, and that the obtained crude crystals were recrystallized from ethanol, to give Compound 39 (369 mg).

Workup

  1. concentrationwas concentrated under reduced pressure, that the residue
custom
was purified by silica gel column chromatography
  • customthat the obtained crude crystals
  • customwere recrystallized from ethanol
  • Sources & evidence

    ORD record
    ord-f3c262c37ecd43e0955d3e99bad2ecf7
    Source dataset
    uspto-grants-1999_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US05952355

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes