反应详情

温度

0 °C

To a mixture of methyl 2-chloro-4-hydroxybenzoate (4.43 g) and 2,6-lutidine (6.64 mL) in DCM (50 mL) cooled with an ice bath was added triisopropylsilyl trifluoromethanesulfonate (7.66 mL). After being stirred at 0° C. for 1 h, saturated aqueous NaHCO3 was added thereto. The mixture was diluted with Et2O and layers were separated. The aqueous layer was extracted with Et2O. The combined organic layer was washed with brine, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane). The product was dissolved in diethyl ether (175 mL). To the solution cooled with an ice bath was added lithium aluminum hydride (1.08 g). After being stirred at 0° C. for 30 min, sodium sulfate decahydrate was added thereto. The mixture was filtered through a pad of celite. The filtrate was concentrated. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (6.87 g).

1. temperaturecooled with an ice bath
2. customwere separated
3. extractionThe aqueous layer was extracted with Et2O
4. washThe combined organic layer was washed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated
7. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)
8. dissolutionThe product was dissolved in diethyl ether (175 mL)
9. temperatureTo the solution cooled with an ice bath
10. additionwas added lithium aluminum hydride (1.08 g)
11. stirringAfter being stirred at 0° C. for 30 min
12. additionsodium sulfate decahydrate was added
13. filtrationThe mixture was filtered through a pad of celite
14. concentrationThe filtrate was concentrated
15. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)