反应详情

温度

60 °C

To a solution of trimethyl(2-methylbut-3-yn-2-yloxy)silane (1.5 g, 9.6 mmol) in tetrahydrofuran (15 mL) was added 4,4,5,5-tetramethyl-1,3,2-dioxaborolane (2.79 mL, 19.2 mmol), followed by 9-BBN dimer (0.117 g, 0.480 mmol). The mixture was heated at 60° C. for 24 hours, then cooled to ambient temperature and quenched by the careful addition of saturated aqueous ammonium chloride solution. The mixture was extracted with ethyl acetate (2×15 mL). The organics were combined, dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, eluted with a gradient of 0-60% ethyl acetate in hexanes) to afford the title compound (600 mg, 22% yield). 1H NMR (300 MHz, DMSO-d6) δ ppm 0.06-0.08 (m, 9H) 1.19 (s, 12H) 1.25 (s, 6H) 5.41 (d, J=17.85 Hz, 1H) 6.53 (d, J=17.85 Hz, 1H); MS (DCI/NH3) m/z 285 (M+H)+.

1. temperaturecooled to ambient temperature
2. customquenched by the careful addition of saturated aqueous ammonium chloride solution
3. extractionThe mixture was extracted with ethyl acetate (2×15 mL)
4. dry with materialdried (Na2SO4)
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by column chromatography
8. washeluted with a gradient of 0-60% ethyl acetate in hexanes)