反应详情

A solution of 6-bromopyridine-2-caboxaldehyde (15.0 g), 1-undecyne (12.9 g), triethylamine (24.5 g), bis(triphenylphosphine)palladium(II)chloride (1.1 g, 2%), and copper(I)iodide (0.15 g, 1%) in dry tetrahydrofuran (60 ml) was heated under nitrogen at 55° C. for 10 hrs. The reaction mixture was filtered, the filter cake was washed with ethyl acetate, and the filtrate was evaporated. The residue was dissolved in ethyl acetate, and the solution was washed with half-saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was flash chromatographed on silica gel, eluting with 0%-2%-ethyl acetate:hexane. The appropriate fractions were collected and evaporated to yield 17.5 g (84.0%) of product.

1. filtrationThe reaction mixture was filtered
2. washthe filter cake was washed with ethyl acetate
3. customthe filtrate was evaporated
4. dissolutionThe residue was dissolved in ethyl acetate
5. washthe solution was washed with half-saturated sodium chloride solution
6. dry with materialdried over anhydrous magnesium sulfate
7. filtrationfiltered
8. concentrationthe filtrate was concentrated
9. customchromatographed on silica gel
10. washeluting with 0%-2%-ethyl acetate
11. customThe appropriate fractions were collected
12. customevaporated