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

HRID 23403

Reaction equation

HRID 23403 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-a4e26d10e9de41e7b1672cfefe6736c6
Source dataset
uspto-grants-2005_02
Patent number
US06852726B2

Linked notes

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