反应详情

Crude 2-{1-[(triisopropylsilyl)oxy]vinyl}pyridine (131.5 g, assumed 0.413 mmol) is placed in a 2 L, 1N round bottom flask and dissolved in anhydrous THF (Aldrich Sure Seal, 0.6 L). The flask is equipped with a reflux condenser and the apparatus is placed under nitrogen. NCS (60.66 g, 0.454 mol, 1.1 eq.) is added and the mixture is heated to reflux and maintained at reflux for 2 hours. The reaction mixture is cooled to room temperature, poured into a 4 L separatory funnel containing ether (1.5 L), and is washed with saturated aq. NaHCO3 (2×0.7 L). The organic phase is separated, dried (Na2SO4), and concentrated in vacuo affords the target (117.5 g) as a yellow-orange oil. The crude material is not further purified, but is immediately carried into the next step.

1. customThe flask is equipped with a reflux condenser
2. temperaturethe mixture is heated
3. temperatureto reflux
4. temperaturemaintained
5. temperatureat reflux for 2 hours
6. additionpoured into a 4 L separatory funnel
7. washis washed with saturated aq. NaHCO3 (2×0.7 L)
8. customThe organic phase is separated
9. dry with materialdried (Na2SO4)
10. concentrationconcentrated in vacuo
11. customaffords the target (117.5 g) as a yellow-orange oil