反应详情

Dissolve sodium metal (0.345 g) in absolute EtOH (25 mL), add diethyloxalate (10 mL) and then add 4-methyl-3-nitrobenzonitrile (1b, m=0, 1.6 g, Aldrich) as an EtOH solution (25 mL). Stir the reaction mixture at rt for 16 hours, neutralize the reaction by addition of 5N HCl (3 mL) and remove the EtOH under reduced pressure. Partition the residue between CH2Cl2 (100 mL) and H2O (50 mL). Wash the organic layer successively with H2O (50 mL) and brine (50 mL), dry (MgSO4) and concentrate to give a crude oil. Purify the oil by chromatography on SiO2 eluting with cyclohexane-EtOAc, 70-30 v/v, to afford gave after drying (40° C., house vacuum), the title compound (1.5 g) as yellow crystals, mp 118° C.

1. customthe reaction
2. customremove the EtOH under reduced pressure
3. customPartition the residue between CH2Cl2 (100 mL) and H2O (50 mL)
4. washWash the organic layer successively with H2O (50 mL) and brine (50 mL)
5. dry with materialdry (MgSO4)
6. concentrationconcentrate
7. customto give a crude oil
8. customPurify the oil by chromatography on SiO2 eluting with cyclohexane-EtOAc, 70-30 v/v
9. customto afford
10. customgave
11. customafter drying (40° C., house vacuum)