Hexanoyl chloride → 3-Hexanoyl-1-tosylindole

HRID 1636195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1636195
[Cl-].[Cl-].[Cl-].[Al+3].[C:5](Cl)(=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[S:13]([N:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1)([C:16]1[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=1)(=[O:15])=[O:14]>ClCCl>[C:5]([C:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:23]([S:13]([C:16]2[CH:22]=[CH:21][C:19]([CH3:20])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:24]=1)(=[O:11])[CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Komponenten

5

Edukt 3

HCID 67340Hexanoyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 10956616N-Tosylindole

Produkt 1

HCID 193502863-Hexanoyl-1-tosylindoleAusbeute 78,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
5 °C

Versuchsvorschrift

Aluminium trichloride (6.01 g, 45.2 mmol), is suspended in dichloromethane (80 cm3), under nitrogen. A solution of hexanoyl chloride (5a) (6.62 g, 49.2 mmol) in dichloromethane (20 cm3) is added slowly to the stirred mixture at ambient temperature. After the addition is complete, the mixture is stirred for a further 10 minutes. The reaction mixture is cooled to 5° C. 1-tosylindole (4) (45.2 mmol, 12.24 g) in dichloromethane (20 cm3) is added to the mixture while the temperature is maintained at 5° C. After two hours stirring at room temperature the reaction mixture is treated with ice water, extracted with dichloromethane and dried over magnesium sulphate. Evaporation of the solvent gives a thick oil, which crystallises in the presence of methanol and dichloromethane to yield colourless crystals of 3-hexanoyl-1-tosylindole (6a) (13.07 g, 35.42 mmol, 78%), m.p. 91-93° C.

Aufarbeitung

  1. additionAfter the addition
  2. temperatureis maintained at 5° C
  3. stirringAfter two hours stirring at room temperature the reaction mixture
  4. extractionextracted with dichloromethane
  5. dry with materialdried over magnesium sulphate
  6. customEvaporation of the solvent
  7. customgives a thick oil, which
  8. customcrystallises in the presence of methanol and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-068146c8dd3a40698e44ae94b7f5bf80
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06033601

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