Reacción #1851

Ecuación de reacción

3-hydroxy-6-hydroxymethyl-2-iodopyridine

potassium acetate

triphenylphosphine

ethyl acrylate

→

Ethyl 3-{3-hydroxy-6-hydroxymethylpyridin2-yl}propenoate

Disolventes

water

DMF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mix was cooled
2. 2
   ExtracciónThe product was extracted into ethyl acetate (3×20 ml)
3. 3
   Lavadothe combined extracts were washed with water (2×15 ml) with brine (15 ml)
4. 4
   Otrodried
5. 5
   Otroevaporated
6. 6
   OtroThe etude product was purified by passage in ethyl acetate through a pad of silica
7. 7
   Otroyielding
8. 8
   Otroafter evaporation a yellow solid (295 g, 47%)
9. 9
   Otromp (B.HCl) 199°-203° C.

Procedimiento

To a solution of 3-hydroxy-6-hydroxymethyl-2-iodopyridine (708 mg, 2.82 mmol) in DMF (5.7 ml) and water (0.3 ml) were added potassium acetate (0.74 g, 7.5 mmol), triphenylphosphine (63 mg, 0.24 mmol), ethyl acrylate (0.98 ml, 0.90 g, 9.0 mmol) and palladium acetate (27 mg, 0.12 mmol). The mixture was placed under nitrogen and stirred and heated at 120° C. for 5 h. The mix was cooled and poured into water (50 ml). The product was extracted into ethyl acetate (3×20 ml) and the combined extracts were washed with water (2×15 ml) with brine (15 ml), dried and evaporated. The etude product was purified by passage in ethyl acetate through a pad of silica, yielding after evaporation a yellow solid (295 g, 47%). mp (B.HCl) 199°-203° C.

Fuente