反应详情

温度

-78 °C

To a 1.0 L three-necked round-bottomed flask was added 50 mL of THF and the reaction mixture was cooled to −78° C. Butyl lithium (BuLi, 1.6 M, 14.4 mL, 23 mmol) was added dropwise keeping the temperature below −70° C. Acetonitrile (1.3 mL, 25 mmol) in 30 mL of THF was added dropwise to the flask amidst stirring and cooling. After 2 hours (h) of stirring, (3,4-dimethoxyphenyl)acetic acid methyl ester (2.3 g, 11 mmol) was added to the resulting white colloidal mixture in the flask. The reaction mixture was stirred for a further 2 h, followed by the addition of saturated ammonium chloride solution (NH4Cl, 75 mL) at −78° C. The organic layer was separated, dried with sodium sulfate (Na2SO4), filtered to remove the drying agent and evaporated to dryness to give the crude product. This crude product was purified by silica gel column chromatography, eluting with 30-70% ethyl acetate (EtOAc) in hexanes to yield 4-(3,4-dimethoxyphenyl)-3-oxo-butyronitrile in the form of a solidifying amber oil, 1.8 g (75%).

1. customthe temperature below −70° C
2. temperaturecooling
3. stirringAfter 2 hours (h) of stirring
4. stirringThe reaction mixture was stirred for a further 2 h
5. customThe organic layer was separated
6. dry with materialdried with sodium sulfate (Na2SO4)
7. filtrationfiltered
8. customto remove the drying agent
9. customevaporated to dryness
10. customto give the crude product
11. customThis crude product was purified by silica gel column chromatography
12. washeluting with 30-70% ethyl acetate (EtOAc) in hexanes