Sodium Hydroxide → HCID 53770388, compound

HRID 1721944Notes

Reaction equation

HRID 1721944 reaction equation
[CH3:1][C:2]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[O:17])[CH3:16])([CH3:4])[CH3:3].[NH:18]1[C:26]2[CH:25]=[CH:24][CH:23]=[C:22]([CH:27]=O)[C:21]=2[CH:20]=[CH:19]1.[OH-].[Na+]>C(O)C.O>[CH3:4][C:2]([NH:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15](=[O:17])[CH:16]=[CH:27][C:22]1[CH:23]=[CH:24][CH:25]=[C:26]2[C:21]=1[CH:20]=[CH:19][NH:18]2)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 333703Indole-4-carboxaldehydeHCID 13691193HCID 13691193, compound

Product 1

HCID 53770388HCID 53770388, compoundYield 89.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 5.4 g of 1-[2-{2-(1,1-dimethylethylamino)-ethoxy}-phenyl]-ethanone in 75 ml of ethanol was added with stirring under an inert atmosphere to a mixture of 3.339 g of indole-4-carboxaldehyde and 6 ml of 50% sodium hydroxide solution and after stirring for 4 hours, the mixture was diluted with water and extracted with ethyl acetate. The organic phase was washed with aqueous sodium chloride solution, dried over a deshydrant and evaporated to dryness under reduced pressure. The residue was chromatographed over silica and eluted with a 9-1 ethyl acetate-triethylamine mixture to obtain 7.41 g of 1-[2-{2-(1,1-dimethylethylamino)-ethoxy}-phenyl]-3-[1H-indol-4-yl]-2-propen-1-one (E).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic phase was washed with aqueous sodium chloride solution
  3. customdried over a deshydrant
  4. customevaporated to dryness under reduced pressure
  5. customThe residue was chromatographed over silica
  6. washeluted with a 9-1 ethyl acetate-triethylamine mixture

Sources & evidence

ORD record
ord-fced496433a144a7ac085896ced93ef4
Source dataset
uspto-grants-1989_08
Patent number
US04853408

Reaction notes

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