تفاعل #52309

معادلة التفاعل

3-bromo-5-methanesulfonyl-pyridine

3,3,3-triethoxypropyne

triethylamine

→

title compound

المردود 87.3%

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

المردود 87.3%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةat reflux for 48 h
2. 2
   أخرىthe solvent was removed under reduced pressure
3. 3
   أخرىThe crude product was chromatographed on silica (30% ethyl acetate/hexanes)

الإجراء التجريبي

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).

المصدر