Sodium sulfate decahydrate → 2-(5-chloro-3-methylsulfanyl-1H-indol-2-yl)-ethanol

HRID 23403

Reaktionsgleichung

Reaktionsgleichung von HRID 23403
C[O:2][C:3](=O)[CH2:4][C:5]1[NH:6][C:7]2[C:12]([C:13]=1[S:14][CH3:15])=[CH:11][C:10]([Cl:16])=[CH:9][CH:8]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>CCOCC>[Cl:16][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[NH:6][C:5]([CH2:4][CH2:3][OH:2])=[C:13]2[S:14][CH3:15]

Komponenten

5

Edukt 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 69545956(5-chloro-3-methylsulfanyl-1H-indol-2-yl)-acetic acid methyl ester

Produkt 1

HCID 225741032-(5-chloro-3-methylsulfanyl-1H-indol-2-yl)-ethanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel2×

Versuchsvorschrift

To a solution of (5-chloro-3-methylsulfanyl-1H-indol-2-yl)-acetic acid methyl ester (0.252 g, 0.93 mmole) in ether (10 ml) was added 0.93 ml of a 1M solution of lithium aluminum hydride in ether at room temperature. The reaction mixture was stirred for 15 minutes, after which time sodium sulfate decahydrate (1 g) was cautiously added. The reaction mixture was stirred for an hour at room temperature, filtered, and the filtrate evaporated to dryness. The crude alcohol was purified by column chromatography (silica gel) using 7:3 hexane:ethyl acetate as the eluting solvent. The pure 2-(5-chloro-3-methylsulfanyl-1H-indol-2-yl)-ethanol was isolated as a pale solid (0.191 g, 84% yield).

Aufarbeitung

  1. stirringThe reaction mixture was stirred for an hour at room temperature
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness
  4. customThe crude alcohol was purified by column chromatography (silica gel)

Quellen und Nachweise

ORD-Eintrag
ord-a4e26d10e9de41e7b1672cfefe6736c6
Quelldatensatz
uspto-grants-2005_02
Patentnummer
US06852726B2

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