反应详情

温度

65 °C

To a suspension of Sodium thiomethoxide (0.42 g, 6 mmol) in DMF (1.2 mL) was added N-{[4-(3-methoxyphenyl)tetrahydro-pyran-4-yl]methyl}-N,N-dimethylamine (0.3 g, 1.2 mmol) and the resulting mixture was heated to 65° C. for 7 h, allowed to cool to ambient temperature and quenched with saturated aqueous NH4Cl (6 mL). The mixture was extracted with DCM, dried over Na2SO4, filtered and concentrated in vacuo to provide 0.25 g of crude product. A mixture of the crude and HBr (3 mL) was heated to reflux for 1 h. After cooling, water was added to quench the reaction and the mixture was basified with NaHCO3 and extracted with DCM. The organic extracts were dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography (DCM/MeOH (10% NH3)) to provide 3-{4-[(dimethylamino)methyl]tetrahydro-pyran-4-yl}phenol (0.100 g, 35.5%).

1. temperatureto cool to ambient temperature
2. customquenched with saturated aqueous NH4Cl (6 mL)
3. extractionThe mixture was extracted with DCM
4. dry with materialdried over Na2SO4
5. filtrationfiltered
6. concentrationconcentrated in vacuo
7. customto provide 0.25 g of crude product
8. temperaturewas heated
9. temperatureto reflux for 1 h
10. temperatureAfter cooling
11. customto quench
12. customthe reaction
13. extractionextracted with DCM
14. dry with materialThe organic extracts were dried over Na2SO4
15. filtrationfiltered
16. concentrationconcentrated
17. customThe residue was purified by flash chromatography (DCM/MeOH (10% NH3))