反应详情

4-(4,4-Dimethyl-3-oxo-cyclohexyl)-3-methyl-benzonitrile (0.6 g, 2.49 mmol) in N,N-dimethylformamide dimethylacetal (50 mL) is stirred at 90° C. for two days. The mixture is cooled to room temperature and concentrated in vacuo. The residue is diluted with ethyl acetate (50 mL) and water (50 mL). The organic phase is separated and the aqueous phase is extracted with ethyl acetate (3×50 mL). The combined organic phase is washed with brine, dried over anhydrous sodium sulfate, and concentrated in vacuo. The residue is purified by silica gel flash chromatography, eluting with pet ether:EtOAc 1:1 to MeOH:DCM=1:30 to give 4-[(2Z)-2-(dimethylaminomethylene)-4,4-dimethyl-3-oxo-cyclohexyl]-3-methyl-benzonitrile (0.2 g, 27%).

1. concentrationconcentrated in vacuo
2. additionThe residue is diluted with ethyl acetate (50 mL) and water (50 mL)
3. customThe organic phase is separated
4. extractionthe aqueous phase is extracted with ethyl acetate (3×50 mL)
5. washThe combined organic phase is washed with brine
6. dry with materialdried over anhydrous sodium sulfate
7. concentrationconcentrated in vacuo
8. customThe residue is purified by silica gel flash chromatography
9. washeluting with pet ether:EtOAc 1:1 to MeOH