反应详情

温度

60 °C

2-Chloro-6-(hydroxymethyl)-4-iodopyridin-3-ol (5.7 g, 20 mmol) is combined with bis (triphenylphosphine) palladium dichloride (1.12 g, 1.6 mmol) in 50 ml DMF under nitrogen. The mixture is treated with tetravinyl tin, is warmed to 60° C. for 6 h followed by 50° C. for 18 h, and at rt for 72 h. The mixture is diluted with 250 ml EtOAc and is extracted with 4×100 ml 2:1:1 water/saturated NaCl/saturated NaHCO3. The organic layer is dried (MgSO4) and is concentrated in vacuo to a yellow oil. The crude material is chromatographed over 200 g SiO2 (230-400 mesh) eluting with 37% EtOAc/hexane. The appropriate fractions are combined and concentrated to afford 1.45 g (39%) of 2-chloro-6-(hydroxymethyl)-4-vinylpyridin-3-ol as a pale yellow solid. MS for C8H8ClNO2 (EI) m/z: 185 (M)+.

1. waitat rt for 72 h
2. extractionis extracted with 4×100 ml 2:1:1 water/saturated NaCl/saturated NaHCO3
3. dry with materialThe organic layer is dried (MgSO4)
4. concentrationis concentrated in vacuo to a yellow oil
5. customThe crude material is chromatographed over 200 g SiO2 (230-400 mesh)
6. washeluting with 37% EtOAc/hexane
7. concentrationconcentrated