反应详情

To a solution of 2-bromo-5-hydroxymethyltoluene (87.4 g) in methylene chloride (350 ml) were added, under ice-cooling with stirring, trietylamine (72.7 ml) and 4-dimethylaminopyridine (DMAP)(500 mg), and then thereto was added t-butyldimethylsilyl chloride (65.5 g). The mixture was stirred at 0° C. for 15 minutes, and stirred at room temperature for 3 hours. The reaction mixture is filtrated, and the filtrate was concentrated under reduced pressure. To the residure was added water (100 ml), and the mixture was extracted with ethyl acetate. The extract was washed with 10% aqueous hydrochloric acid solution, water, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and the solvent was distilled away. The residue was purified by a reduced pressure distillation (110° C. to 115° C./0.4 mmHg) to give the title compound (127.5 g).

1. temperaturecooling
2. stirringThe mixture was stirred at 0° C. for 15 minutes
3. stirringstirred at room temperature for 3 hours
4. filtrationThe reaction mixture is filtrated
5. concentrationthe filtrate was concentrated under reduced pressure
6. additionTo the residure was added water (100 ml)
7. extractionthe mixture was extracted with ethyl acetate
8. washThe extract was washed with 10% aqueous hydrochloric acid solution, water, saturated aqueous sodium hydrogencarbonate solution and saturated aqueous sodium chloride solution
9. dry with materialdried over anhydrous magnesium sulfate
10. distillationthe solvent was distilled away
11. distillationThe residue was purified by a reduced pressure distillation (110° C. to 115° C./0.4 mmHg)