反应详情

A mixture of 3.00 g (24.4 mmol) 1-but-3-enyl-1H-[1,2,3]triazole, 6.79 g (20.3 mmol) tert-butyl-(4-iodo-phenoxy)-dimethyl-silane, 1.07 g (4.06 mmol) triphenylphosphine, 0.685 g (3.05 mmol) palladium(II)acetate and 56 ml triethylamine was heated to reflux for 24 h. The reaction mixture was cooled to r.t., evaporated, stirred with ice and adjusted to pH=1 by addition of conc. HCl. The organic material was collected with ethyl acetate/dichloromethane 1:2, the organic phase dried over sodium sulfate and evaporated. The residue was stirred with 20.3 ml 1M solution of tetrabutylammonium fluoride solution in THF at 28° C. for 3 h. After removal of THF, the residue was dissolved in dichloromethane, washed with water, evaporated and purified by chromatography on silica gel (ethyl acetate/n-heptane 5:1). The product containing fractions were collected, evaporated and stirred with little ethyl acetate/n-heptane 3:1 to yield 1.53 g (29%).

1. temperaturewas heated
2. temperatureto reflux for 24 h
3. customevaporated
4. additionadjusted to pH=1 by addition of conc. HCl
5. customThe organic material was collected with ethyl acetate/dichloromethane 1:2
6. dry with materialthe organic phase dried over sodium sulfate
7. customevaporated
8. stirringThe residue was stirred with 20.3 ml 1M solution of tetrabutylammonium fluoride solution in THF at 28° C. for 3 h
9. customAfter removal of THF
10. dissolutionthe residue was dissolved in dichloromethane
11. washwashed with water
12. customevaporated
13. custompurified by chromatography on silica gel (ethyl acetate/n-heptane 5:1)
14. additionThe product containing fractions
15. customwere collected
16. customevaporated
17. stirringstirred with little ethyl acetate/n-heptane 3:1
18. customto yield 1.53 g (29%)