反应详情

温度

80 °C

To a 200 mL round-bottom flask, 3.49 g of 2-bromopyridine-6-methanol, 3.0 g of t-butyl 4-pentynoate, 190 mg of BHT, 1.17 g of copper(I) iodide, 877 mg of tetrakis(triphenylphosphine)palladium(0), 2.72 g of t-butylamine and 56 mL of DMF were added, and the mixture was stirred under argon atmosphere at 80° C. for 6 hours. After the DMF was removed under reduced pressure from the reaction mixture, saturated aqueous sodium bicarbonate was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, and then the solvent was removed. The residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=2:1) to give 2.76 g of t-butyl 5-(6-hydroxymethylpyridin-2-yl)pent-4-ynoate as a yellow oil.

1. customAfter the DMF was removed under reduced pressure from the reaction mixture, saturated aqueous sodium bicarbonate
2. additionwas added
3. extractionthe mixture was extracted with ethyl acetate
4. washThe organic layer was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customthe solvent was removed
7. customThe residue was purified by chromatography on silica gel (n-hexane-ethyl acetate=2:1)