3',4',5'-Trimethoxyacetophenone → (E)-3-(5-Benzyloxyindol-3-yl)-1-(3,4,5-trimethoxy-phenyl)-2-propen-1-one

HRID 618108Notes

Reaction equation

HRID 618108 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].[CH2:16]([O:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[C:27]2[CH:33]=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[CH2:16]([O:23][C:24]1[CH:25]=[C:26]2[C:30](=[CH:31][CH:32]=1)[NH:29][CH:28]=[C:27]2/[CH:33]=[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])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

3

Reactant 2

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 813985-(phenylmethoxy)-1H-indole-3-carbaldehyde

Product 1

HCID 21850297(E)-3-(5-Benzyloxyindol-3-yl)-1-(3,4,5-trimethoxy-phenyl)-2-propen-1-oneYield 2.4%

Procedure

Substantially the same procedure as in Example 1 was repeated using 3',4',5'-trimethoxyacetophenone (2.1 g) and 5-benzyloxyindole-3-carboxaldehyde (2.51 g) except that the obtained crude crystals were recrystallized twice from acetone, to give Compound 28 (107 mg).

Workup

  1. customobtained crude crystals
  2. customwere recrystallized twice from acetone

Sources & evidence

ORD record
ord-3402290872e44530833925195aa0c80c
Source dataset
uspto-grants-1999_09
Patent number
US05952355

Reaction notes

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