반응 #162369

반응 방정식

2-Fluoro-3-[(trimethylsilyl)ethynyl]pyridine

tetra-n-butylammonium fluoride

→

desired product

수율 86.2%

3-ethynyl-2-fluoropyridine

수율 86.2%

용매

tetrahydrofuran

water

THF

반응 조건

후처리

1. 1
   추출The reaction was extracted with ethyl acetate
2. 2
   세척the combined organic extracts were washed with brine (3×)
3. 3
   건조dried over MgSO4
4. 4
   농축concentrated
5. 5
   기타The crude was purified via column chromatography on silica gel (10% ethyl acetate:90% hexanes)

실험 절차

2-Fluoro-3-[(trimethylsilyl)ethynyl]pyridine (8.8 g, 0.046 mol) was dissolved in a mixture of tetrahydrofuran (20 mL) and water (2 mL). A 1.0 M solution of tetra-n-butylammonium fluoride (12 g, 0.046 mol) in THF (46 ml) was then added dropwise at 0° C., and the reaction mixture was stirred for 1 hour. The reaction was extracted with ethyl acetate, and the combined organic extracts were washed with brine (3×), dried over MgSO4 and concentrated. The crude was purified via column chromatography on silica gel (10% ethyl acetate:90% hexanes) to provide 4.8 g of the desired product. 1H NMR (400 MHz, CDCl3): δ 8.20 (m, 1H), 7.88-7.92 (m, 1H), 7.17-7.21 (m, 1H), 3.40 (s, 1H).

출처