Toluene → 1-Benzyl-3-phenylsulfinylindole

Participants

Reaction Steps

A mixture of toluene (100 ml), 50% sodium hydroxide (20 ml), 3-phenylsulfinylindole (4.27 g, 17.7 mmol) and benzyltrimethylammonium chloride (6.01 g, 26.5 mmol) was vigorously stirred at reflux temperature for 4 hours. The organic phase was separated and combined with an ether extract of the aqueous phase. The extract was dried and evaporated in vacuo giving a solid which on crystallization from dichloromethane-hexane gave the solid product. Chromatography of the mother liquor on silica gel using hexane-ethyl acetate (3:2) as the eluant gave a further quantity of the title compound, m.p. 148°-149° C. identical to the material prepared in Example 8.

Provenance & Evidence