Reaktion #1851

Reaktionsgleichung

3-hydroxy-6-hydroxymethyl-2-iodopyridine

potassium acetate

triphenylphosphine

ethyl acrylate

→

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

Lösungsmittel

water

DMF

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mix was cooled
2. 2
   ExtraktionThe product was extracted into ethyl acetate (3×20 ml)
3. 3
   Waschenthe combined extracts were washed with water (2×15 ml) with brine (15 ml)
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated
6. 6
   SonstigeThe etude product was purified by passage in ethyl acetate through a pad of silica
7. 7
   Sonstigeyielding
8. 8
   Sonstigeafter evaporation a yellow solid (295 g, 47%)
9. 9
   Sonstigemp (B.HCl) 199°-203° C.

Vorschrift

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.

Quelle