Iodoethane → HCID 13799993, compound

Participants

Reaction Steps

11.9 g (37.8 mmol) of 4-(1-hydroxyethyl)-1-tosyl indole in 150 ml of methylene chloride was mixed at room temperature under argon with 13.3 g (85 mmol) of ethyl iodide, 6.7 g of tetrabutylammonium hydrogen sulfate and 6.7 g (119.3 mmol) of pulverized potassium hydroxide one after the other. The solution was stirred for 2 hours. After filtration over silica gel, the solution was again mixed with equal amounts of ethyl iodide, tetrabutylammonium hydrogen sulfate and potassium hydrogen oxide. The reaction mixture was stirred for 2 hours at room temperature, washed with 200 ml of water and the organic phase dried, filtered and concentrated. Subsequent chromatography on silica gel with cyclohexane/ethyl acetate (8:2) yielded 8.5 g of 4-(1-ethoxyethyl)-1-tosyl indole as oil.

Provenance & Evidence