Isopropyl iodide → 5-Isopropoxy-1H-indole

HRID 2240532Notes

Reaction equation

HRID 2240532 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].[CH:17](I)([CH3:19])[CH3:18]>C(#N)C>[CH:17]([O:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2)([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 160545-Hydroxyindole

Product 1

HCID 167380545-Isopropoxy-1H-indoleYield 83%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 5-hydroxyindole 23 (2.0 g, 0.015 mol) in 20 ml of acetonitrile, anhydrous potassium carbonate (4 grams, 0.028 mol) was added and stirred vigorously before isopropyl iodide (3 grams, 0.018 mol) was added. The reaction was stirred for 2 days at room temperature and the solid was washed with acetonitrile. The filtrate was concentrated and purified with flash-chromatography (80% n-hexane/20% ethyl acetate) to give the desired product 24 as a light-yellowish oil (1.72 g, 83%; M+1=176.1).

Workup

  1. additionwas added
  2. washthe solid was washed with acetonitrile
  3. concentrationThe filtrate was concentrated
  4. custompurified with flash-chromatography (80% n-hexane/20% ethyl acetate)

Sources & evidence

ORD record
ord-164bf4561dfa4b6796a08c4e1eedd023
Source dataset
uspto-grants-2010_05
Patent number
US07723374B2

Reaction notes

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