Ethylene Oxide → 2-[3-Methyl-1-(phenylsulfonyl)indol-2-yl]ethanol

Participants

Reaction Conditions

Reaction Steps

To a solution of lithium diisopropylamide prepared from diisopropylamine (1.11 g) and n-butyllithium (1.61 M in hexane; 7.0 ml), in dry tetrahydrofuran under nitrogen atmosphere at -70° C. was added dropwise over 20 minutes a solution of 3-methyl-1-phenylsulfonylindole (2.71 g) in tetrahydrofuran (20 ml). The mixture was stirred for 1 hour below -70° C. and then allowed to warm slowly to 0° C. over 1 hour. The resulting solution was cooled to -70° C. and then treated with ethylene oxide (484 mg) in dry tetrahydrofuran (5 ml). The mixture was stirred for 1 hour below -70° C. and then allowed to warm slowly to room temperature over 3 hours. After stirring overnight, the reaction mixture was treated with cold water and extracted twice with ethyl acetate. The combined extracts were washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was chromatographed over silica gel (eluted with 5% ethyl acetate in toluene) to give 2-[3-methyl-1-(phenylsulfonyl)indol-2-yl]ethanol (1.19 g).

Provenance & Evidence