Ethyl Acetate → 5-(Trifluoromethoxy)-1H-indole

HRID 367368

Reaction equation

HRID 367368 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:7][C:8]([F:22])([F:21])[O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=O)[C:13]2=O.[O-]S([O-])(=O)=O.[Na+].[Na+].C(OCC)(=O)C>C1COCC1>[F:22][C:8]([F:7])([F:21])[O:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24436Sodium SulfateHCID 27327525-(trifluoromethoxy)-2,3-dihydro-1H-indole-2,3-dioneHCID 21226445Aluminium lithium hydride

Product 1

HCID 179890505-(Trifluoromethoxy)-1H-indoleYield 23.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (10.4 mL, 1M in THF, 10.4 mmol) was added to a solution of 5-trifluoromethoxyisatin (0.8 g, 3.45 mmol) in THF at room temperature and the mixture was refluxed overnight. The reaction mixture was cooled, and Na2SO4 10H2O was added very carefully portionwise, followed by ethyl acetate. The reaction mixture was then filtered, and the filtrate was evaporated. The residual oil was purifed by column chromatography with ethyl acetate in hexanes (2:98) to yield 5-trifluoromethoxy-1H-indole (0.162 g, 23%).

Workup

  1. temperaturethe mixture was refluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe reaction mixture was then filtered
  4. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-db4b385c5414493e9da7264059cc4606
Source dataset
uspto-grants-2000_10
Patent number
US06133287

Linked notes

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