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

Temperatur

120 °C

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.

1. temperatureThe mix was cooled
2. extractionThe product was extracted into ethyl acetate (3×20 ml)
3. washthe combined extracts were washed with water (2×15 ml) with brine (15 ml)
4. customdried
5. customevaporated
6. customThe etude product was purified by passage in ethyl acetate through a pad of silica
7. customyielding
8. customafter evaporation a yellow solid (295 g, 47%)
9. custommp (B.HCl) 199°-203° C.

ORD-Eintrag

ord-33f5c2c61cec497c9cae12b9bafc104f

Quelldatensatz

uspto-grants-1998_03

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05726315