Реакция #1851

Уравнение реакции

3-hydroxy-6-hydroxymethyl-2-iodopyridine

potassium acetate

triphenylphosphine

ethyl acrylate

→

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

Растворители

water

DMF

water

Условия реакции

Обработка

1. 1
   ТемператураThe mix was cooled
2. 2
   ЭкстракцияThe product was extracted into ethyl acetate (3×20 ml)
3. 3
   Промывкаthe combined extracts were washed with water (2×15 ml) with brine (15 ml)
4. 4
   Другоеdried
5. 5
   Другоеevaporated
6. 6
   ДругоеThe etude product was purified by passage in ethyl acetate through a pad of silica
7. 7
   Другоеyielding
8. 8
   Другоеafter evaporation a yellow solid (295 g, 47%)
9. 9
   Другоеmp (B.HCl) 199°-203° C.

Методика

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.

Источник