反応 #1851

反応方程式

3-hydroxy-6-hydroxymethyl-2-iodopyridine

potassium acetate

triphenylphosphine

ethyl acrylate

→

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

溶媒

water

DMF

water

反応条件

後処理

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

実験手順

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.

出典