Indole → 1H-Indole, 1-(1-methoxyethyl)-

HRID 427768Notes

Reaction equation

HRID 427768 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.Cl[CH:13]([O:15][CH3:16])[CH3:14]>CN(C=O)C>[CH3:16][O:15][CH:13]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4]1)[CH3:14]

Participants

5

Reactant 3

HCID 798IndoleHCID 24758Sodium hydrideHCID 1370671-Chloro-1-methoxyethane

Product 1

HCID 315761H-Indole, 1-(1-methoxyethyl)-Yield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (1.92 gm of a 60% dispersion in oil) in 75 mL of DMF was added indole (4.68 gm, 40 mmol) (Aldrich). The mixture was stirred for 15 minutes at 0° C., and 1-chloroethyl methylether (4 mL) was added dropwise. The resulting mixture was stirred at 0° C. for 1 hour and poured over ice/water, and extracted with toluene. The organic layer was dried over magnesium sulfate, and evaporated. The residue was purified by flash chromatography using EtOAc/hexanes to give 4 gm of 1-[1-methoxyethyl]indole. (Yield 58%).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 1 hour
  2. extractionextracted with toluene
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-fda5e46a6cce4fcdb4ebce9c540d39c0
Source dataset
uspto-grants-2001_11
Patent number
US06313143B1

Reaction notes

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