Water → n-Methanesufonyl-6-carbomethoxyindole

Participants

Reaction Steps

A solution of NaN(TMS)2 (1 M) in THF (11 mmol, 11 ml) was added dropwise to a -78° C solution of 6-carbomethoxyindole (876 mg, 5 mmol, prepared according to the procedure of Batcho, et al., Org. Synth. Coll. 7:34) in dry THF (10 ml). After stirring for 30 min, MeSO2Cl (1.47 mL) (Me=CH3) was added. The mixture was allowed to stir overnight then poured onto 100 ml of water. The mixture was extracted with CH2Cl2 (2×75 ml). The extracts were washed with brine, dried (Na2SO4), and the solvent was removed by rotary evaporation to give a light brown solid. The solid was purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane) to give 510 mg of N-methanesulfonyl-6-carbomethoxyindole.

Provenance & Evidence