Potassium Hydroxide → 5-(Propan-2-yl)-1H-indole

HRID 610052Notes

Reaction equation

HRID 610052 reaction equation
[OH-].[K+].[CH:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11](C(=O)C(F)(F)F)[CH:10]=[CH:9]2)([CH3:5])[CH3:4]>CO>[CH:3]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[NH:11][CH:10]=[CH:9]2)([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 105629375-Isopropyl-1-trifluoroacetylindole

Product 1

HCID 105589185-(Propan-2-yl)-1H-indoleYield 98.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of potassium hydroxide in methanol (5% w/v, 17 mL) containing 5-isopropyl-1-trifluoroacetylindole (Example 2a, 1.163 g, 4.55 mmol) was stirred at room temperature overnight. After removal of the methanol, the product was partitioned between ethyl acetate and water, washed sequentially with water and brine, and dried over sodium sulfate. Flash chromatography (silica, 10% ethyl acetate in hexanes) yielded 5-isopropyl-1H-indole (715 mg, 98%).

Workup

  1. customAfter removal of the methanol
  2. customthe product was partitioned between ethyl acetate and water
  3. washwashed sequentially with water and brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-bf621d480c944ce29b8038f0e17b6a75
Source dataset
uspto-grants-1999_12
Patent number
US05998462

Reaction notes

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