反应详情

A solution of 2-naphthol (2.28 g, 15.8 mmol) in 20 ml of diethylether was treated with sodium hydride (60% mineral oil dispersion, 0.632 g, 15.8 mmol) and the mixture was stirred at ambient temperature for 20 minutes. Methanesulfonyl chloride (0.677 ml, 8.7 mmol) was added dropwise to an ice bath cooled solution of [1-(4-bromo-2,6-dimethyl-phenyl)-3,5-diethyl-1H-pyrazol-4-yl]-methanol (2.68 g, 7.9 mmol) and triethylamine (1.38 ml, 9.9 mmol) in diethylether (25 ml). The mixture was stirred at 0°-5° C. for 15 minutes; and then stirred at ambient temperature for 20 minutes. The mixture was then added to the above-described sodium 2-napthoxide suspension. After 16 hours stirring at ambient temperature, the reaction mixture was extracted with methylene chloride/dilute aqueous sodium bicarbonate (150 ml and 100 ml, respectively). The aqueous phase was extracted twice with 50 ml portions of methylene chloride. The combined organic extracts were dried over anhydrous sodium sulfate and concentrated in vacuo to an oil (5.65 g). Trituration of the entire sample with ethyl acetate/hexanes (5 ml and 45 ml, respectively) followed by filtration afforded the title compound 1.15 g as a colorless solid.

1. stirringThe mixture was stirred at 0°-5° C. for 15 minutes
2. stirringand then stirred at ambient temperature for 20 minutes
3. stirringAfter 16 hours stirring at ambient temperature
4. extractionthe reaction mixture was extracted with methylene chloride/dilute aqueous sodium bicarbonate (150 ml and 100 ml
5. extractionThe aqueous phase was extracted twice with 50 ml portions of methylene chloride
6. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
7. concentrationconcentrated in vacuo to an oil (5.65 g)
8. filtrationTrituration of the entire sample with ethyl acetate/hexanes (5 ml and 45 ml, respectively) followed by filtration