Water → HCID 10773594, compound

HRID 1899000Notes

Reaction equation

HRID 1899000 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2.I[CH2:14][CH2:15][CH3:16].O>CN(C=O)C>[CH2:14]([O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)[CH2:15][CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 160545-HydroxyindoleHCID 24758Sodium hydrideHCID 336431-Iodopropane

Product 1

HCID 10773594HCID 10773594, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (0.99 g, 50% in oil) was added to dry DMF (5 ml) and the resulting suspension was stirred at room temperature. A solution of 5-hydroxyindole (2.5 g) in dry DMF (15 ml) was added dropwise and a dark purple solution formed. After stirring the mixture for 30 min, 1-iodopropane (3.51 g) was added, and the resulting mixture was stirred at room temperature for 3 h. The mixture was poured into water and extracted with ether (3x). The combined extracts were washed with water, dried (MgSO4) and evaporated to dryness to give a crude residue which was purified by chromatography (SiO2 ; hexane/ether). 5-n-Propyloxyindole was obtained as a yellow oil (2.03 g).

Workup

  1. customa dark purple solution formed
  2. stirringAfter stirring the mixture for 30 min
  3. stirringthe resulting mixture was stirred at room temperature for 3 h
  4. extractionextracted with ether (3x)
  5. washThe combined extracts were washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness
  8. customto give a crude residue which
  9. customwas purified by chromatography (SiO2 ; hexane/ether)

Sources & evidence

ORD record
ord-7130b2c35b644fad8be3089148eb68b8
Source dataset
uspto-grants-1996_11
Patent number
US05571833

Reaction notes

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