반응 #48061

반응 방정식

2-chloro-4-trimethylsilanylethynyl-pyridine

TBAF

NH4Cl

→

2-chloro-4-ethynyl-pyridine

수율 91.1%

용매

THF

THF

반응 조건

후처리

1. 1
   기타the THF was removed under reduced pressure
2. 2
   추출The aqueous mixture was extracted with diethylether
3. 3
   세척the combined organic extracts were washed with water and brine
4. 4
   건조dried (Na2SO4)
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The remaining residue was purified by column chromatography (pentane/diethylether 100:0 to 4:1)

실험 절차

To a solution of 2.389 g of 2-chloro-4-trimethylsilanylethynyl-pyridine (11.39 mmol) in THF (90 ml) were added 11.39 ml of a 1 M TBAF solution in THF at −78° C. and the reaction mixture was stirred for 45 min at 0° C. Then saturated NH4Cl solution was added and the THF was removed under reduced pressure. The aqueous mixture was extracted with diethylether and the combined organic extracts were washed with water and brine, dried (Na2SO4), filtered and concentrated in vacuo. The remaining residue was purified by column chromatography (pentane/diethylether 100:0 to 4:1) to give 2-chloro-4-ethynyl-pyridine (1.427 g, 91%) as an off-white solid. 1H-NMR (CDCl3, 300 MHz: δ 3.36 (s, 1H), 7.27 (dd, J=5 and 1 Hz, 2H), 7.40 (br s, 1H), 8.37 (d, J=8 Hz, 2H).

출처