3-(1-Ethoxyvinyl)-4-Methylpyridine synthesis

Yield:486414-68-0 91%

Reaction Conditions:

tetrakis(triphenylphosphine) palladium⁽⁰⁾ in toluene; for 4 h;Heating / reflux;

Steps:

A.59.1 [0470] Step 1. 3-(1-Ethoxy-vinyl)-4-methyl-pyridine

[0471] 3-Bromo-4-methyl-pyridine (2.46 g, 14.3 mmol; Emka Chemie), tributyl-(1-ethyoxyvinyl)-stannane (6.20 g, 17.2 mmol), and tetrakis(triphenylphosphine)-palladium(0) (1.32 g, 1.14 mmol) stirred in dry toluene (50 ml) at reflux under argon for 4 hours. The mixture was concentrated in vacuo and purified by column chromatography (25% EtOAc/hexanes) to give 2.12 g of a clear oil in 91% yield, which was used without any further purification. [0472] 1H NMR: δ 8.50 (s, 1H), 8.40 (d, 1H, J=5.1 Hz), 7.08 (s, 1H, J=5.1 Hz), 4.38 (d, 1H, J=2.4 Hz), 4.24 (d, 1H, J=2.4 Hz), 3.91 (q, 2H, J=7.2 Hz), 2.37 (s, 31H), 1.38 (t, 31H, J=7.2 Hz).

References:

US2003/225147,2003,A1 Location in patent:Page 35