Reacción #1850

Ecuación de reacción

3-hydroxy-2-iodo-6-methylpyridine

potassium acetate

triphenylphosphine

ethyl acrylate

→

Ethyl (3-hydroxy-6-methylpyridin-2-yl)propenoate

Disolventes

DMF

water

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe mixture was cooled
2. 2
   Filtraciónfiltered
3. 3
   workup.ADDITIONadded to water (100 ml)
4. 4
   ExtracciónThe product was extracted into ethyl acetate (3×30 ml)
5. 5
   LavadoThe combined extracts were washed with water (2×25 ml) and with brine (25 ml)
6. 6
   Secadodried over sodium sulphate
7. 7
   Otroevaporated
8. 8
   workup.WAITThis left a tan solid

Procedimiento

To a solution of 3-hydroxy-2-iodo-6-methylpyridine (1.175 g, 5.0 mmol) in DMF (9.5 ml) and water (0.5 ml) were added potassium acetate (1.23 g, 12.5 mmol), triphenylphosphine (105 mg, 0.40 mmol), palladium chloride (36 mg, 0.20 mmol) and ethyl acrylate (1.63 ml, 1.50 g, 15.0 mmol). The mixture was placed under nitrogen and heated at 120° C. for 1.5 h. The mixture was cooled, filtered from deposited palladium black, and added to water (100 ml). The product was extracted into ethyl acetate (3×30 ml). The combined extracts were washed with water (2×25 ml) and with brine (25 ml), then dried over sodium sulphate and evaporated. This left a tan solid, the product (951 mg, 91%). mp 192°-195° C. (dec)

Fuente