反应 #1851

反应方程式

3-hydroxy-6-hydroxymethyl-2-iodopyridine

potassium acetate

triphenylphosphine

ethyl acrylate

→

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

溶剂

water

DMF

water

反应条件

后处理

1. 1
   温度The mix was cooled
2. 2
   萃取The product was extracted into ethyl acetate (3×20 ml)
3. 3
   洗涤the combined extracts were washed with water (2×15 ml) with brine (15 ml)
4. 4
   其他dried
5. 5
   其他evaporated
6. 6
   其他The etude product was purified by passage in ethyl acetate through a pad of silica
7. 7
   其他yielding
8. 8
   其他after evaporation a yellow solid (295 g, 47%)
9. 9
   其他mp (B.HCl) 199°-203° C.

实验过程

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.

来源