反应详情

温度

2.5 °C

To a solution of 6-(benzyloxy)pyridin-3-ol (2.0 g, 10 mmol, 1 eq.) in DMF (20 mL) was added NaH (60% in mineral oil; 0.6 g, 15 mmol, 1.5 eq.) at 0-5° C. portion-wise. Upon the completion of addition, the mixture was continued to stir at 0-5° C. for 15 min, added chloromethyl methyl ether (0.88 g, 11 mmol, 1.1 eq.), stirred at 0-5° C. for another 20 min, and quenched with NH4Cl(sat) solution. The aqueous layer was extracted with EtOAc (3×20 mL) and the combined organic layers were washed with water and brine, dried over Na2SO4, concentrated, and purified on silica gel using 25% EtOAc/hexanes as eluent to give 2-(benzyloxy)-5-(methoxymethoxy)pyridine (2.1 g, 87%) as a colorless oil. LRMS (M+H+) m/z 246.1

1. additionUpon the completion of addition
2. stirringstirred at 0-5° C. for another 20 min
3. customquenched with NH4Cl(sat) solution
4. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
5. washthe combined organic layers were washed with water and brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated
8. custompurified on silica gel using 25% EtOAc/hexanes as eluent