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

HRID 1382840Notes

Reaction equation

HRID 1382840 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].C([N+](CC)(CC)CC1C=CC=CC=1)C>C(O)C.O>[OH:1][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[C:16](=[O:17])[CH:15]=[CH:12][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:6]=1[CH:5]=[CH:4][NH:3]2

Participants

7

Reactant 4

HCID 14797Potassium HydroxideHCID 17208BenzyltriethylammoniumHCID 68490alpha-HydroxyacetophenoneHCID 333703Indole-4-carboxaldehyde

Product 1

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

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
30 °C

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-e9adc636d8a742e89eadb4d6d6fa0517
Source dataset
uspto-grants-1989_02
Patent number
US04808609

Reaction notes

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