Sodium Hydroxide → 2-methyl-5-(methylthio)-1H-indole

HRID 400612Notes

Reaction equation

HRID 400612 reaction equation
C1(S([N:10]2[C:18]3[C:13](=[CH:14][C:15]([S:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH3:21])(=O)=O)C=CC=CC=1.[OH-].[Na+]>C(O)C.[Cl-].[Na+].O>[CH3:21][C:11]1[NH:10][C:18]2[C:13]([CH:12]=1)=[CH:14][C:15]([S:19][CH3:20])=[CH:16][CH:17]=2

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 695719351h-Indole,2-methyl-5-(methylthio)-1-(phenylsulfonyl)-

Product 1

HCID 110412692-methyl-5-(methylthio)-1H-indoleYield 71.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 1-benzenesulfonyl-2-methyl-5-methylsulfanyl-1H-indole (156 mg, 0.49 mmol) in 10 mL of ethanol was added 10 mL of 10% aqueous sodium hydroxide solution. The mixture was warmed at reflux for 18 hours. The mixture was then diluted with 10 mL of brine and extracted with three 20 mL portions of ethyl acetate. The combined organic layers were washed with two 10 mL portions of 10% aqueous sodium hydroxide solution, two 20 mL portions of saturated aqueous ammonium chloride, two 20 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude product was adsorbed onto silica gel and chromatographed on silica gel using ethyl acetate-hexanes (1:99, then 2:98, then 3:97, then 5:96) to afford 62 mg (71.2% yield) of 2-methyl-5-methylsulfanyl-1H-indole.

Workup

  1. temperatureThe mixture was warmed
  2. temperatureat reflux for 18 hours
  3. extractionextracted with three 20 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with two 10 mL portions of 10% aqueous sodium hydroxide solution, two 20 mL portions of saturated aqueous ammonium chloride, two 20 mL portions of brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customchromatographed on silica gel

Sources & evidence

ORD record
ord-809ad9df85b04f2790c7c5d5e47290ae
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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