反应详情

4.66 g (19.23 mmol) of methyl α-hydroxy-α-phenyl-p-toluate was dissolved in 50 ml of N,N-dimethylformamide. 0.77 g (19.23 mmol) of 60% sodium hydride was added thereto and the mixture was stirred at room temperature for 1 hour. 3.10 g (28.85 mmol) of 2-dimethylaminoethyl chloride was added thereto and the mixture was heated at 80° C. for 2.5 hours. After the reaction mixture was cooled and poured into water, the obtained mixture was extracted twice with ethyl acetate and the extract was washed with brine, and dried (MgSO4). The solvent was distilled off and the resulting residue was purified by silica gel column chromatography (chloroform:methanol=40:1 (v/v)) to obtain 0.53 g (1.69 mmol) of methyl α-(2-dimethylaminoethoxy)-α-phenyl-p-toluate as a brown oily substance. Its spectroscopic data are as follows:

1. temperaturethe mixture was heated at 80° C. for 2.5 hours
2. temperatureAfter the reaction mixture was cooled
3. extractionthe obtained mixture was extracted twice with ethyl acetate
4. washthe extract was washed with brine
5. dry with materialdried (MgSO4)
6. distillationThe solvent was distilled off
7. customthe resulting residue was purified by silica gel column chromatography (chloroform:methanol=40:1 (v/v))