反应详情

0.66 g (16.5 mmols) of sodium hydride and 2.6 g (15.0 mmols) of 4-tert-butylphenylacetonitrile were suspended in 50 ml of tetrahydrofuran. To the suspension was added dropwise 1.95 g (16.5 mmols) of dimethyl carbonate dissolved in 10 ml of tetrahydrofuran while stirring at room temperature. The mixture was refluxed with heating for 2 hours, and the solvent was distilled off under reduced pressure. Water was added to the residue, and the residue was acidified by diluted hydrochloric acid and twice extracted with 30 ml of ethyl acetate. The ethyl acetate extraction solutions were mixed, washed with a saturated brine solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. The residue thus-obtained was purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1), giving 1.8 g of the desired product (yield 52%)

1. temperatureThe mixture was refluxed
2. temperaturewith heating for 2 hours
3. distillationthe solvent was distilled off under reduced pressure
4. additionWater was added to the residue
5. extractiontwice extracted with 30 ml of ethyl acetate
6. extractionThe ethyl acetate extraction solutions
7. additionwere mixed
8. washwashed with a saturated brine solution
9. dry with materialdried over anhydrous magnesium sulfate
10. distillationThe solvent was distilled off under reduced pressure
11. customThe residue thus-obtained
12. customwas purified by silica gel column chromatography (n-hexane:ethyl acetate=2:1)