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

HRID 1721952Notes

Reaction equation

HRID 1721952 reaction equation
[OH-:1].[K+].[NH:3]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([CH:12]=O)[C:6]=2[CH:5]=[CH:4]1.O[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:17]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.C(O)C.O>[NH:3]1[C:11]2[C:6](=[C:7]([CH:12]=[CH:15][C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[OH:1])=[O:17])[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 68490alpha-HydroxyacetophenoneHCID 333703Indole-4-carboxaldehyde

Product 1

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

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

0.5 ml of a 38% potassium hydroxide solution was added with stirring at 30° C. under an inert atmosphere to a mixture of 0.132 g of indol-4-carboaldehyde, 0.1 ml of 2-hydroxy-acetophenone and 0.189 g of triethylbenzyl ammonium chloride in 2 ml of ethanol and after stirring at 30° for 23 hours, the mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over a deshydrant and evaporated to dryness. The residue was chromatographed over silica and eluted with methylene chloride to obtain 159 mg of 3-(1H-indol-4-yl)-1-(2-hydroxy-phenyl)-2-propen-1-one melting at ≃164° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with water
  3. customdried over a deshydrant
  4. customevaporated to dryness
  5. customThe residue was chromatographed over silica
  6. washeluted with methylene chloride

Sources & evidence

ORD record
ord-cf5d62f9628f4d9aba32d09948b8af86
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

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