Sodium Chloride → (E)-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxopent-4-enoic acid methyl ester

HRID 352092Notes

Reaction equation

HRID 352092 reaction equation
[CH3:1][O:2][C:3](=[O:28])/[CH:4]=[C:5](\C)/[CH:6]=[CH:7][C:8]1[N:9]([CH:24]([CH3:26])[CH3:25])[C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[OH-:29].[NH4+].[Cl-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:28])[CH2:4][C:5](=[O:29])/[CH:6]=[CH:7]/[C:8]1[N:9]([CH:24]([CH3:26])[CH3:25])[C:10]2[C:15]([C:16]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14923Ammonium HydroxideHCID 86589178(E)-5-[3-(4-Fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-methylpenta-2,4-dienoic Acid Methyl Ester

Product 1

HCID 11326444(E)-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-oxopent-4-enoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.63 g (1.49 mmol) of (E)-5-[3-(4-fluorophenyl)-1-isopropyl-1H-indol-2-yl]-3-methylpenta-2,4-dienoic acid methyl ester in 20 ml of THF are introduced into a 50 ml round-bottomed flask equipped with a magnetic stirrer and nitrogen delivery line, 4 ml of 1N ammonium hydroxide solution are added, and the mixture is stirred for 6 hours at room temperature. The reaction mixture is poured into 200 ml of saturated sodium chloride solution and extracted twice with 100 ml of ethyl acetate, and the organic phase is washed three times with 50 ml of water, dried over magnesium sulfate, filtered and concentrated by evaporation. The crude product is purified by means of flash chromatography (hexane/ethyl acetate=9:1). An orange resin is obtained which, according to NMR, is the product in a keto-enol equilibrium of approximately 3:1.

Workup

  1. customequipped with a magnetic stirrer
  2. extractionextracted twice with 100 ml of ethyl acetate
  3. washthe organic phase is washed three times with 50 ml of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation
  7. customThe crude product is purified by means of flash chromatography (hexane/ethyl acetate=9:1)
  8. customAn orange resin is obtained which

Sources & evidence

ORD record
ord-0f2a7907756b457b96c5d328bd3793ea
Source dataset
uspto-grants-2004_06
Patent number
US06743926B2

Reaction notes

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