1-(2-Hydroxyphenyl)-3-(1H-indol-4-yl)prop-2-en-1-one → 1-(2-Hydroxyphenyl)-3-(1H-indol-4-yl)propan-1-one

HRID 1721953Notes

Reaction equation

HRID 1721953 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([CH:10]=[CH:11][C:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[OH:20])=[O:13])[CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1>CO>[OH:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[C:12](=[O:13])[CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:4]=1[CH:3]=[CH:2][NH:1]2

Participants

3

Reactant 1

HCID 538459351-(2-Hydroxyphenyl)-3-(1H-indol-4-yl)prop-2-en-1-one

Product 1

HCID 137856631-(2-Hydroxyphenyl)-3-(1H-indol-4-yl)propan-1-oneYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 200 mg of the product of Step A in 10 ml of methanol was hydrogenated in the presence of palladized carbon until absorption ceased and was then filtered. Chromatography over silica and elution with a 6-3-1 cyclohexane-dichloromethane-triethylamine mixture yielded 143 mg of 1-[2-hydroxy-phenyl]-3-[1H-indol-4-yl]-1-propanone melting at 143° C.

Workup

  1. customwas hydrogenated in the presence of palladized carbon until absorption
  2. filtrationwas then filtered
  3. washChromatography over silica and elution with a 6-3-1 cyclohexane-dichloromethane-triethylamine mixture

Sources & evidence

ORD record
ord-b6f7df3dd22b42308c2cc6704c78f325
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

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