반응 #51980

반응 방정식

2-{1-[(triisopropylsilyl)oxy]vinyl}pyridine

NCS

ether

→

2-{2-chloro-1-[(triisopropylsilyl)oxy]ethenyl}pyridine

용매

THF

반응 조건

후처리

1. 1
   기타The flask is equipped with a reflux condenser
2. 2
   온도the mixture is heated
3. 3
   온도to reflux
4. 4
   온도maintained
5. 5
   온도at reflux for 2 hours
6. 6
   workup.ADDITIONpoured into a 4 L separatory funnel
7. 7
   세척is washed with saturated aq. NaHCO3 (2×0.7 L)
8. 8
   기타The organic phase is separated
9. 9
   건조dried (Na2SO4)
10. 10
    농축concentrated in vacuo
11. 11
    기타affords the target (117.5 g, 91%) as a yellow-orange oil

실험 절차

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, 91%) as a yellow-orange oil. The crude material is not further purified, but is immediately carried into the next step.

출처