Water → HCID 10773594, compound

Participants

Reaction Steps

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).

Provenance & Evidence