Indole → 1-(2-methoxyethyl)-1H-indole

HRID 1009009Notes

Reaction equation

HRID 1009009 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1.I[CH2:13][CH2:14][O:15][CH3:16]>CN(C=O)C>[CH3:16][O:15][CH2:14][CH2:13][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1

Participants

5

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 791361-Iodo-2-methoxyethane

Product 1

HCID 212839961-(2-methoxyethyl)-1H-indoleYield 92.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a slurry of sodium hydride (0.932 g, 23.0 mmol) in DMF (30 mL) was added indole (2.52 g, 21 mmol) portionwise at 10-20° C. over 5 minutes. The reaction mixture was stirred at rt for 1.5 h, and 2-iodoethylmethylether (4.8 g, 26 mmol) in DMF (10 mL) was added over 5 minutes. The mixture was stirred at rt for 2 h, quenched with ice/water, and extracted with tert-butylmethylether. The organics were washed, dried, and concentrated. The residue was chromatographed on silica gel using heptane/ethyl acetate as eluent to obtain 1-(2-methoxy-ethyl)-1H-indole (3.40 g) as a yellowish liquid. MS (ISP): m/e 176.4 (M+H)+

Workup

  1. stirringThe mixture was stirred at rt for 2 h
  2. customquenched with ice/water
  3. extractionextracted with tert-butylmethylether
  4. washThe organics were washed
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-f4f0cfb97c37457da57f6f73f70d2ee3
Source dataset
uspto-grants-2011_07
Patent number
US07973051B2

Reaction notes

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