反应详情

温度

10 °C

Combined 3,4-dimethoxy-phenyl-acetonitrile (20.0 g, 113 mmol) and THF (100 mL). Cooled in a dry-ice/acetone bath. Added dropwise, sodium bis(trimethylsilyl)amide (226 mL, 1.0M in THF, 226 mmol, 2 eq.). After the addition was complete, allowed to warm to 10 ° C. Cooled in a dry-ice/acetone bath. Added dropwise, ethyl bromoacetate (37.7 g, 226 mmol). After the addition was complete, the reaction mixture was allowed to warm to ambient temperature and maintained overnight. Filtered the reaction mixture and concentrated in vacuo to obtain a residue. The residue was partitioned between diethyl ether (600 mL) and water (200 mL). The organic layer was extracted with water (200 mL), saturated NH4Cl (2×100 mL), dried over MgSO4, filtered, and concentrated in vacuo to obtain a residue. Chromatographed on silica gel eluting with ethyl acetate/hexane (1:2) to obtain the title compound: Rf =0.42 (silica gel, 1:2 ethyl acetate/hexane).

1. temperatureCooled in a dry-ice/acetone bath
2. additionAdded dropwise
3. additionAfter the addition
4. temperatureCooled in a dry-ice/acetone bath
5. additionAdded dropwise
6. additionAfter the addition
7. temperatureto warm to ambient temperature
8. temperaturemaintained overnight
9. filtrationFiltered the reaction mixture
10. concentrationconcentrated in vacuo
11. customto obtain a residue
12. customThe residue was partitioned between diethyl ether (600 mL) and water (200 mL)
13. extractionThe organic layer was extracted with water (200 mL), saturated NH4Cl (2×100 mL)
14. dry with materialdried over MgSO4
15. filtrationfiltered
16. concentrationconcentrated in vacuo
17. customto obtain a residue
18. customChromatographed on silica gel eluting with ethyl acetate/hexane (1:2)