反应详情

To 3-bromophenylacetonitrile (7.55 g, 38.5 mmol) and 1,3-dibromo-2,2-dimethyoxypropane (10.09 g, 38.5 mmol) in dry DMSO (100 ml) was added in two portions sodium hydride (3.23 g of 60% dispersion in oil, 81 mmol) while the mixture was cooled in a water bath. The mixture was stirred at RT for 10 minutes, and heated at 60° C. in an oil bath for 6 hours. The reaction was diluted with water and extracted with EtOAc. The organic layer was separated, washed with water and the solvent removed. The residual red oil was eluted through a short pad of silica, eluent 10% EtOAc/Hexane. The resulting ketal was dissolved in acetone (100 ml) and 1N aqueous HCl (10 ml) and heated at reflux for 6 hours under a nitrogen atmosphere. The solvent was removed and the residue was neutralized by treatment with aqueous NaHCO3 and extracted with EtOAc. The solvent was removed and the residue was chromatographed (SiO2, eluent 10% EtOAc in hexane) to give a yellow oil which solidified on drying under vacuum.

1. temperaturewas cooled in a water bath
2. temperatureheated at 60° C. in an oil bath for 6 hours
3. extractionextracted with EtOAc
4. customThe organic layer was separated
5. washwashed with water
6. customthe solvent removed
7. washThe residual red oil was eluted through a short pad of silica, eluent 10% EtOAc/Hexane
8. dissolutionThe resulting ketal was dissolved in acetone (100 ml)
9. temperature1N aqueous HCl (10 ml) and heated
10. temperatureat reflux for 6 hours under a nitrogen atmosphere
11. customThe solvent was removed
12. extractionextracted with EtOAc
13. customThe solvent was removed
14. customthe residue was chromatographed (SiO2, eluent 10% EtOAc in hexane)
15. customto give a yellow oil which
16. customon drying under vacuum