反应详情

Dissolve 1-{2-[4-(6-benzyloxy-2-bromo-1-oxo-1H-1λ4-benzo[b]thiophen-3-yloxy)-phenoxy]-ethyl}-piperidine (22.36 g, 40.3 mmol) in methanol (160 mL) and chloroform (80 mL). Add a 30% solution of titanium trichloride in aqueous HCl (31.4 mL, 80.6 mmol) and stir at ambient temperature for 2 hours. Quench reaction mixture with saturated aqueous sodium bicarbonate (500 mL) and dilute with dichloromethane (500 mL). Separate layers and wash the organic layer with saturated aqueous sodium bicarbonate (500 mL), water (500 mL), and brine (500 mL). Dry with sodium sulfate, filter and concentrate in vacuo. Chromatograph the residue on a SiO2 column eluting with methanol (containing 10% NH4OH) in dichloromethane (0 to 2%) to give 19.2 g of the title compound (88%).

1. customQuench
2. customreaction mixture with saturated aqueous sodium bicarbonate (500 mL)
3. washSeparate layers and wash the organic layer with saturated aqueous sodium bicarbonate (500 mL), water (500 mL), and brine (500 mL)
4. dry with materialDry with sodium sulfate
5. filtrationfilter
6. concentrationconcentrate in vacuo
7. washChromatograph the residue on a SiO2 column eluting with methanol (containing 10% NH4OH) in dichloromethane (0 to 2%)