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

HRID 618103Notes

Reaction equation

HRID 618103 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][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2[CH:26]=O>>[CH3:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][CH:21]=[C:20]2/[CH:26]=[CH:14]/[C:13]([C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:15]

Participants

3

Reactant 2

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 2591875-Methylindole-3-carboxaldehyde

Product 1

HCID 21850200(E)-3-(5-Methylindol-3-yl)-1-(3,4,5-trimethoxyphenyl)-2-propen-1-oneYield 33%

Procedure

Substantially the same procedure as in Example 1 was repeated using 3',4',5'-trimethoxyacetophenone (2.1 g) and 5-methylindole-3-carboxaldehyde (1.59 g) 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 a mixed solvent of ethyl acetate and hexane, to give Compound 20 (1.16 g).

Workup

  1. concentrationwas concentrated under reduced pressure, that the residue
  2. customwas purified by silica gel column chromatography
  3. customthat the obtained crude crystals
  4. customwere recrystallized from a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-bea4a375c27e417298094c00713b9be3
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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