Iodoethane → 5-Ethoxy-1H-indole

HRID 41061

Reaction equation

HRID 41061 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+].I[CH2:18][CH3:19].ClCCl.CO>CC(C)=O>[CH2:18]([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]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 160545-Hydroxyindole2×HCID 21226129Dichloromethane methanol

Product 1

HCID 47776675-Ethoxy-1H-indoleYield 90%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of commercially available 5-hydroxy-indole (18 g, 13.5 mmol), anhydrous K2CO3 (93.5 g, 5 equiv) and iodoethane (40.5 ml, 3.75 equiv) in acetone (180 mL) is stirred at 50° C. under argon. When TLC (dichloromethane-methanol, 95:5) indicates the disappearance of 5-hydroxy-indole (4 days), the mixture is filtered, the solid is washed with acetone, then the filtrate is concentrated to give 17.67 g (90%) of the title compound, which is sufficiently pure to be used in the next step. M.p. 144-146° C. (from ethanol).

Workup

  1. filtrationthe mixture is filtered
  2. washthe solid is washed with acetone
  3. concentrationthe filtrate is concentrated

Sources & evidence

ORD record
ord-7954df6899c24f36acc08db5c4700c76
Source dataset
uspto-grants-2013_09
Patent number
US08530493B2

Linked notes

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