反应详情

224 mg of 4-[N(4-methoxyphenyl)amino]benzonitrile was dissolved in 1.2 ml of N,N-dimethylformamide, and 48 mg of sodium borohydride was added thereto under cooling with ice, followed by stirring at room temperature for 30 minutes. The previously prepared 4-(t-butyldimethylsilyloxy)benzyl chloride was dissolved in 1.2 ml of N,N- dimethylformamide and added to the reaction mixture under cooling with ice, followed by stirring at room temperature for 2 days. After water was added to the reaction mixture, the product was extracted with ethyl acetate. After the extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 1.2 ml of tetrahydrofuran, and 1.2 ml of a 1 M tetrahydrofuran solution of tetrabutylammonium fluoride was added thereto, followed by stirring at room temperature for 15 minutes. After a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, the product was extracted with ethyl acetate. After the extract was washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (using ethyl acetate as the eluent) to obtain 229 mg of 4-[N-(4-hydroxybenzyl)-N-(4-methoxyphenyl)amino]benzonitrile.

1. temperatureunder cooling with ice
2. additionadded to the reaction mixture
3. temperatureunder cooling with ice
4. stirringby stirring at room temperature for 2 days
5. extractionthe product was extracted with ethyl acetate
6. washAfter the extract was washed with water
7. dry with materialdried over anhydrous sodium sulfate
8. distillationthe solvent was distilled off under reduced pressure
9. dissolutionThe resulting residue was dissolved in 1.2 ml of tetrahydrofuran
10. addition1.2 ml of a 1 M tetrahydrofuran solution of tetrabutylammonium fluoride was added
11. stirringby stirring at room temperature for 15 minutes
12. additionAfter a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture
13. extractionthe product was extracted with ethyl acetate
14. washAfter the extract was washed with water
15. dry with materialdried over anhydrous sodium sulfate
16. distillationthe solvent was distilled off under reduced pressure
17. customThe resulting crude product was purified by silica gel column chromatography (