Reaction #1851

Reaction equation

3-hydroxy-6-hydroxymethyl-2-iodopyridine

potassium acetate

triphenylphosphine

ethyl acrylate

→

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

Solvents

water

DMF

water

Conditions

Workup

1. 1
   TemperatureThe mix was cooled
2. 2
   ExtractionThe product was extracted into ethyl acetate (3×20 ml)
3. 3
   Washthe combined extracts were washed with water (2×15 ml) with brine (15 ml)
4. 4
   Otherdried
5. 5
   Otherevaporated
6. 6
   OtherThe etude product was purified by passage in ethyl acetate through a pad of silica
7. 7
   Otheryielding
8. 8
   Otherafter evaporation a yellow solid (295 g, 47%)
9. 9
   Othermp (B.HCl) 199°-203° C.

Procedure

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