Propionyl chloride → HCID 19808783, compound

Participants

Reaction Conditions

Reaction Steps

3.00 g of 5-methoxy-1-methoxymethylindole was dissolved in 15 ml of anhydrous tetrahydrofuran. Thereto was dropwise added 11.0 ml of 1.5 M n-butyllithium hexane solution, in 5 minutes with stirring at -30° C. The resulting mixture was stirred at 0° C. for 30 minutes. This solution was dropwise added to a solution of 1.59 g of propionyl chloride dissolved in 15 ml of anhydrous tetrahydrofuran, in 30 minutes with stirring at -60° C. The reaction mixture was stirred at room temperature for 10 minutes, and then was added to 50 ml of an aqueous saturated sodium hydrogencarbonate solution in one portion. Thereto was added 150 ml of ethyl acetate. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography (eluant: toluene/ethyl acetate=50/1) to obtain 1.34 g (yield: 35%) of 5-methoxy-1-methoxymethyl-2-propionylindole as a light yellow oily material.

Provenance & Evidence