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

Participants

Reaction Conditions

Reaction Steps

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, 7.5mmol), triphenylphosphine (63 mg, 0.24 mmol), ethyl amylate (0.98 ml, 0.90g, 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 (3×20ml) and the combined extracts were washed with water (2×15 ml) with brine (15 ml), dried and evaporated. The crude 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.

Provenance & Evidence