反应详情

0.5 M 3-fluorophenylmagnesium bromide solution in THF (3, 750 ml, 375 mmol) was added to a solution of 8-dimethylamino-1,4-dioxa-spiro[4.5]decane-8-carbonitrile (19.8 g, 94 mmol) in THF (100 ml) in the course of 15 min, under argon and while cooling with ice, and the mixture was then stirred at room temperature for 16 h. For working up of the reaction mixture, saturated ammonium chloride solution (150 ml) and water (60 ml) was added, while cooling with ice, and the mixture was extracted with diethyl ether (3×100 ml). The organic phase was extracted by shaking with water (50 ml) and saturated NaCl solution (50 ml) and the extract was concentrated. A brown oil (26.5 g) remained which, apart from the phenyl compound 4, still contained the ketal 2. The crude product was dissolved in ethyl methyl ketone (156 ml), and ClSiMe3 (17.8 ml, 141 mmol) was added, while cooling with ice. After a reaction time of 6 h, it was possible to isolate the hydrochloride in a yield of 55% (16.3 g) as a white solid with a melting point of 275-278° C.

1. temperaturewhile cooling with ice
2. additionwas added
3. temperaturewhile cooling with ice
4. extractionthe mixture was extracted with diethyl ether (3×100 ml)
5. extractionThe organic phase was extracted
6. stirringby shaking with water (50 ml) and saturated NaCl solution (50 ml)
7. concentrationthe extract was concentrated
8. dissolutionThe crude product was dissolved in ethyl methyl ketone (156 ml)
9. temperaturewhile cooling with ice
10. customAfter a reaction time of 6 h, it