Reaktion #52309

Reaktionsgleichung

3-bromo-5-methanesulfonyl-pyridine

3,3,3-triethoxypropyne

triethylamine

→

title compound

Ausbeute 87.3%

3-Methanesulfonyl-5-triethoxyprop-1-ynyl-pyridine

Ausbeute 87.3%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturat reflux for 48 h
2. 2
   Sonstigethe solvent was removed under reduced pressure
3. 3
   SonstigeThe crude product was chromatographed on silica (30% ethyl acetate/hexanes)

Vorschrift

A solution of 3-bromo-5-methanesulfonyl-pyridine (1.00 g, 4.20 mmol), 3,3,3-triethoxypropyne (1.75 g, 9.4 mmol), dichlorobis(triphenylphospine)palladium(II) (0.15 g, 0.21 mmol), copper(I)iodide (0.08 g, 0.42 mmol), triethylamine (1.80 mL, 12.7 mmol) and dichloromethane (40 mL) was heated at reflux for 48 h. The mixture was cooled to room temperature and the solvent was removed under reduced pressure. The crude product was chromatographed on silica (30% ethyl acetate/hexanes) to give the title compound (1.2 g, 87% yield) as yellow solid. 1H NMR (CDCl3) δ 9.08(d, 1H, J=2.4 Hz), 8.91 (d, 1H J=2.0), 8.28 (t, 1H, J=2.0 Hz), 3.75 (q, 6H, J=7.2), 3.13 (s, 3H), 1.29 (t, 9H, J=7.2).

Quelle