Iodoethane → 1H-Indole, 1-ethyl-2-methyl-

HRID 574597Notes

Reaction equation

HRID 574597 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2.[OH-].[K+].I[CH2:14][CH3:15]>CS(C)=O>[CH2:14]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH:10]=[C:2]1[CH3:1])[CH3:15]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 72242-MethylindoleHCID 14797Potassium Hydroxide

Product 1

HCID 1704321H-Indole, 1-ethyl-2-methyl-Yield 83%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a mixture of 0.20 g (1.52 mmol) of 2-methylindole, 0.38 g (6.89 mmol) of KOH in DMSO (6 mL) was added 0.24 mL (3.04 mmol) of iodoethane. The mixture was stirred at room temperature for 12 hours, quenched by the addition of 15 mL of H2O, and extracted with ethyl acetate (2×15 mL). The combined organic extracts were washed with water (10 mL), brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (ether/petroleum ether 0.5:9.5) to give 0.20 g (83%) of the desired product as a red oil.

Workup

  1. customquenched by the addition of 15 mL of H2O
  2. extractionextracted with ethyl acetate (2×15 mL)
  3. washThe combined organic extracts were washed with water (10 mL), brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by column chromatography (ether/petroleum ether 0.5:9.5)

Sources & evidence

ORD record
ord-bc47e7387dca4e8682b7c2ea05c8bab5
Source dataset
uspto-grants-2015_05
Patent number
US09034895B2

Reaction notes

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