Indole → 1H-Indole-1-ethanol

HRID 1421181Notes

Reaction equation

HRID 1421181 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH2:12]1[O:14][CH2:13]1>CN(C=O)C>[OH:14][CH2:13][CH2:12][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 6354Ethylene OxideHCID 24758Sodium hydride

Product 1

HCID 137349961H-Indole-1-ethanol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

11.7 g of indole in 500 ml of DMF were treated with 4 g of sodium hydride dispersed in mineral oil. After 1 hour the mixture was cooled in an ice bath and 10 ml of ethylene oxide were added. The mixture was allowed to warm to room temperature and was then stirred for 2 hours. The solvent was evaporated and the residue was treated with 50 ml of water and neutralized with 2M hydrochloric acid. The product was extracted into dichloromethane, the solvent was evaporated and the residue was chromatographed with ethyl acetate/petroleum ether to give 7.6 g of 1-(2-hydroxyethyl)indole.

Workup

  1. additiondispersed in mineral oil
  2. temperatureAfter 1 hour the mixture was cooled in an ice bath
  3. customThe solvent was evaporated
  4. additionthe residue was treated with 50 ml of water and neutralized with 2M hydrochloric acid
  5. extractionThe product was extracted into dichloromethane
  6. customthe solvent was evaporated
  7. customthe residue was chromatographed with ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-4d9d47f3e62446b892960a982f80b551
Source dataset
uspto-grants-2000_06
Patent number
USRE036736

Reaction notes

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