반응 #607447

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DIAD

3-bromo-6-methyl-5-nitro-pyridin-2-ol

2,2,2-trifluoro-1-[4-(trifluoromethyl)phenyl]ethanol

triphenylphosphine

→

title compound

수율 41.0%

5-Bromo-2-methyl-3-nitro-6-[2,2,2-trifluoro-1-[4-(trifluoromethyl)phenyl]ethoxy]pyridine

수율 41.0%

용매

THF

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후처리

1. 1
   workup.ADDITIONwere added at room temperature under inert atmosphere (Ar)
2. 2
   기타the temperature below 40° C
3. 3
   기타was consumed
4. 4
   기타to reach room temperature
5. 5
   기타before quenching with water (10 mL)
6. 6
   추출The water phase was extracted with ethyl acetate (2×50 mL)
7. 7
   세척The organic layer was washed with brine (20 mL)
8. 8
   건조dried over anhydrous Na2SO4
9. 9
   여과filtered
10. 10
    기타The solvent was removed in vacuo
11. 11
    기타to give a brown residue, which
12. 12
    기타was purified by combiflash column chromatography (silica gel, heptane/ethyl acetate, v/v=95/5)
13. 13
    workup.ADDITIONFractions containing the pure compound
14. 14
    기타were collected
15. 15
    농축concentrated in vacuo

실험 절차

To a stirring suspension of 3-bromo-6-methyl-5-nitro-pyridin-2-ol (0.25 g, 1.07 mmol) in THF (7 mL), 2,2,2-trifluoro-1-[4-(trifluoromethyl)phenyl]ethanol (0.39 g, 1.61 mmol, 1.5 equiv) and triphenylphosphine (0.42 g, 1.61 mmol, 1.5 eq) were added at room temperature under inert atmosphere (Ar). To this mixture, DIAD (diisopropyl diazodicarboxylate) (0.33 mL, 1.61 mmol, 1.5 eq) was added dropwise over 10 minutes while keeping the temperature below 40° C. The reaction mixture was stirred for 6 h under heating at 60° C. After this time, TLC indicted that the starting material was consumed and the reaction mixture was allowed to reach room temperature before quenching with water (10 mL). The water phase was extracted with ethyl acetate (2×50 mL). The organic layer was washed with brine (20 mL), dried over anhydrous Na2SO4 and filtered. The solvent was removed in vacuo to give a brown residue, which was purified by combiflash column chromatography (silica gel, heptane/ethyl acetate, v/v=95/5). Fractions containing the pure compound were collected and concentrated in vacuo to give the title compound (0.18 g, 41% yield) as a yellow oil.

출처