Benzylsulfonic acid → 5-(Phenylmethoxy)-1-phenylsulfonylindole

Participants

Reaction Steps

DCM (200 mL) was added to 5-benzyloxoindole (15 g, 67 mmol), benzylsulfonic acid (17.8 g, 101 mmol) and tetrabutyl ammoniumsulfat (6.84 g, 20 mmol) followed by 5 M NaOH (40 mL). The reaction mixture was stirred at rt for 3 h. The aqueous layer was washed with DCM (2×30 mL) and the organic layers were combined and washed with brine (30 mL). Drying (MgSO4) and concentration in vacco was followed by crystallization from MeOH to give the product in 83% yield (20.3 g).

Provenance & Evidence