Réaction #1851

Équation de réaction

3-hydroxy-6-hydroxymethyl-2-iodopyridine

potassium acetate

triphenylphosphine

ethyl acrylate

→

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

Solvants

water

DMF

water

Conditions de réaction

Traitement

1. 1
   TempératureThe mix was cooled
2. 2
   ExtractionThe product was extracted into ethyl acetate (3×20 ml)
3. 3
   Lavagethe combined extracts were washed with water (2×15 ml) with brine (15 ml)
4. 4
   Autredried
5. 5
   Autreevaporated
6. 6
   AutreThe etude product was purified by passage in ethyl acetate through a pad of silica
7. 7
   Autreyielding
8. 8
   Autreafter evaporation a yellow solid (295 g, 47%)
9. 9
   Autremp (B.HCl) 199°-203° C.

Mode opératoire

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.

Source