反应详情

温度

70 °C

benzyl cyanoacetate (3.50 g; 20 mmol) is added to a suspension of potassium carbonate (6.08 g; 44 mmol) in 5 mL of DMF. The carbonate is washed with 2 mL of DMF. A solution of 3-nitro-4-chlorotoluene (3.41 g, 20 mmol) in 5 mL of DMF is added and the resulting reaction mixture is stirred at 70° C. for 24 hours. After cooling down to ambient temperature, it is treated with a 5N aqueous solution of HCl (12.5 mL). The mixture is divided between ether (100 mL) and water (50 mL) then the organic phase is re-extracted with ether. The ethereal phases are washed with water, dried over anhydrous MgSO4, filtered under vacuum and evaporated. The residue is purified by chromatography on silica gel (eluent: CH2Cl2/pentane, 1/1) in order to produce benzyl 2-cyano-2-(2-nitro-4-methylphenyl)ethanoate with a yield of 75%.

1. washThe carbonate is washed with 2 mL of DMF
2. customthe resulting reaction mixture
3. temperatureAfter cooling down to ambient temperature
4. extractionthe organic phase is re-extracted with ether
5. washThe ethereal phases are washed with water
6. dry with materialdried over anhydrous MgSO4
7. filtrationfiltered under vacuum
8. customevaporated
9. customThe residue is purified by chromatography on silica gel (eluent: CH2Cl2/pentane, 1/1) in order