反应详情

Sodium hydride (0.31 g, 7.0 mmol) was added to a solution of 3.0 g (5.82 mmol) of the title compound produced in step (i) of Reference Example 12 in N,N-dimethylformamide (19.1 ml), and the mixture was stirred at room temperature for 30 min. Thereafter, 1.65 g (5.82 mmol) of tert-butyl(2-iodoethoxy)dimethylsilane was added thereto, and the mixture was stirred at 100° C. for 21 hr. The reaction was stopped by adding sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure. Methanol (48 ml) was added to the concentrate, 11.6 ml (11.6 mmol) of 1 N hydrochloric acid was added thereto, and the mixture was stirred at room temperature for 30 min. Sodium hydrogencarbonate was added to stop the reaction, and methanol as the solvent was removed under the reduced pressure, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate and was then filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by column chromatography on silica gel (chloroform:methanol=100:1) to give 2.22 g (yield 68%) of the title compound.

1. stirringthe mixture was stirred at 100° C. for 21 hr
2. extractionthe mixture was extracted with ethyl acetate
3. washThe organic layer was washed with water and saturated brine in that order
4. dry with materialwas dried over anhydrous sodium sulfate
5. filtrationwas then filtered
6. concentrationThe filtrate was concentrated under the reduced pressure
7. additionwas added
8. stirringthe mixture was stirred at room temperature for 30 min
9. customwas removed under the reduced pressure
10. extractionfollowed by extraction with ethyl acetate
11. washThe organic layer was washed with water and saturated brine in that order
12. dry with materialwas dried over anhydrous sodium sulfate
13. filtrationwas then filtered
14. concentrationThe filtrate was concentrated under the reduced pressure
15. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=100:1)