1-Butanol → Butyl (5,6-dichloro-1H-indol-3-yl)acetate

HRID 1382120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1382120
Cl.[Cl:2][C:3]1[CH:4]=[C:5]([NH:10]N)[CH:6]=[CH:7][C:8]=1[Cl:9].C[CH:13](C)[CH2:14][CH2:15][C:16]([OH:18])=[O:17].[CH2:20]([OH:24])[CH2:21][CH2:22][CH3:23].[OH-].[Na+]>O>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[C:5]2[C:4]=1[C:14]([CH2:15][C:16]([O:18][CH3:20])=[O:17])=[CH:13][NH:10]2.[Cl:9][C:8]1[CH:7]=[C:6]2[C:5](=[CH:4][C:3]=1[Cl:2])[NH:10][CH:23]=[C:22]2[CH2:21][C:20]([O:17][CH2:16][CH2:15][CH2:14][CH3:13])=[O:24]

Komponenten

7

Edukt 4

HCID 2631-ButanolHCID 12587Isocaproic acidHCID 14798Sodium HydroxideHCID 3084323(3,4-Dichlorophenyl)hydrazine monohydrochloride

Produkt 2

HCID 14391419Butyl (5,6-dichloro-1H-indol-3-yl)acetateHCID 14406773Methyl 4,5-dichloroindole-3-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

With 5.81 g of 3,4-dichlorophenylhydrazine hydrochloride was mixed 11.57 g of 4,4-dimethylbutyric acid, and the resulting mixture was sufficiently stirred to obtain a transparent solution, after which 7.64 g of n-butanol was added. The mixed solution was stirred with treating at 110 C. for 1 hour. The reaction solution was cooled to room temperature, diluted with water, and neutralized with a 1N aqueous sodium hydroxide solution. The aqueous phase was extracted with ethyl acetate, and the ethyl acetate phase was washed with distilled water and a saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was removed by distillation and the oily substance thus obtained was purified by a silica gel column chromatography and a silica gel thin-layer chromatography to obtain 0.28 g of methyl 4,5-dichloroindole-3-acetate and 0.395 g of n-butyl 5,6-dichloroindole-3-acetate.

Aufarbeitung

  1. customto obtain a transparent solution
  2. stirringThe mixed solution was stirred
  3. additionwith treating at 110 C
  4. extractionThe aqueous phase was extracted with ethyl acetate
  5. washthe ethyl acetate phase was washed with distilled water
  6. dry with materiala saturated aqueous sodium chloride solution, and dried over anhydrous sodium sulfate
  7. customThe solvent was removed by distillation
  8. customthe oily substance thus obtained
  9. customwas purified by a silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a31317243d9f464b975019bf3b1c2c42
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04806143

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