تفاعل #1851

معادلة التفاعل

3-hydroxy-6-hydroxymethyl-2-iodopyridine

potassium acetate

triphenylphosphine

ethyl acrylate

→

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

المذيبات

water

DMF

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةThe mix was cooled
2. 2
   استخلاصThe product was extracted into ethyl acetate (3×20 ml)
3. 3
   غسيلthe combined extracts were washed with water (2×15 ml) with brine (15 ml)
4. 4
   أخرىdried
5. 5
   أخرىevaporated
6. 6
   أخرىThe etude product was purified by passage in ethyl acetate through a pad of silica
7. 7
   أخرىyielding
8. 8
   أخرىafter evaporation a yellow solid (295 g, 47%)
9. 9
   أخرىmp (B.HCl) 199°-203° C.

الإجراء التجريبي

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.

المصدر