反应详情

温度

0 °C

A solution of diisopropylazadicarboxylate (1.65 g, 8.16 mmol) in anhydrous tetrahydrofuran (5 mL) was added, dropwise, at 0° C., to a solution of 4-chloro-2-nitrophenol (0.75 g, 4.32 mmol), 4-(tert-butyl-dimethyl-silanyloxy)-cyclohexanol (1.2 g, 5.21 mmol) and triphenylphosphine (2.27 g, 8.65 mmol) in anhydrous tetrahydrofuran (10 mL). The resulting mixture was stirred at 0° C. for 1 hour and at room temperature overnight. The reaction mixture was then sonicated for 20 minutes at room temperature and for 30 minutes at 40° C. and then was stirred at room temperature for 24 hours. The solvent was evaporated under reduced pressure and the residue was partitioned between ethyl acetate and an aqueous solution of sodium bicarbonate (5%), the organic layer was separated and the aqueous layer was extracted 3 times with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The yellow oily residue was purified on a silica gel plug (hexane/EtOAc, from 99/1 to 90/10) to give a yellow oil. This material was dissolved in a mixture of ethyl acetate and hexane (1/1) and the resulting solution was washed twice with an aqueous solution of sodium hydroxide (3 M) and once with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give 1.28 g (79% yield) of tert-butyl-[4-(4-chloro-2-nitro-phenoxy)-cyclohexyloxy]-dimethyl-silane as a light yellow oil.

1. customat 0° C.
2. customThe reaction mixture was then sonicated for 20 minutes at room temperature and for 30 minutes at 40° C.
3. stirringwas stirred at room temperature for 24 hours
4. customThe solvent was evaporated under reduced pressure
5. customthe residue was partitioned between ethyl acetate
6. customan aqueous solution of sodium bicarbonate (5%), the organic layer was separated
7. extractionthe aqueous layer was extracted 3 times with ethyl acetate
8. washThe combined organic extracts were washed with brine
9. dry with materialdried over anhydrous sodium sulfate
10. filtrationfiltered
11. customevaporated under reduced pressure
12. customThe yellow oily residue was purified on a silica gel plug (hexane/EtOAc, from 99/1 to 90/10)
13. customto give a yellow oil
14. washthe resulting solution was washed twice with an aqueous solution of sodium hydroxide (3 M) and once with brine
15. dry with materialdried over anhydrous sodium sulfate
16. filtrationfiltered
17. customevaporated under reduced pressure