反应详情

To 5-benzyloxy-6-methoxyindole (5.0 g, 20 mmol), benzenesulfonyl chloride (5.2 g, 30 mmol) and tetrabutylammonium hydrogen sulfate (2.0 g, 6 mmol) DCM (200 mL) and 4M NaOH (50 mL) were added. The reaction mixture was allowed to stir at room temperature over night. The organic layer was collected and the aqueous phase was washed with DCM (2×30 mL). The combined organic layers were then washed with brine (2×50 mL). Drying, (MgSO4), filtration and evaporation afforded a brown oil. The product precipitated when adding diethyl ether. Recrystallization from MeOH afforded the title compound in 84% yield (6.55 g) as light yellow crystals. MS (ESI+) for C22H19NO4S m/z 394 (M+H)+.

1. customThe organic layer was collected
2. washthe aqueous phase was washed with DCM (2×30 mL)
3. washThe combined organic layers were then washed with brine (2×50 mL)
4. customDrying
5. filtration, (MgSO4), filtration and evaporation
6. customafforded a brown oil
7. customThe product precipitated when
8. additionadding diethyl ether
9. customRecrystallization from MeOH