反应详情

Methyl (acetylamino)(dimethoxyphosphoryl)acetate (2.34 g, 9.8 mmol) is dissolved in CHCl3 (40 mL), treated with DBU (1.46 mL, 9.8 mmol), stirred for 5 min then added dropwise to a 0° C. solution of furan-2,3-dicarbaldehyde (1.65 g, 8.9 mmol) in CHCl3 (80 mL). The mixture is stirred for 2.5 h as the cooling bath expires then 5.5 h at RT and finally 24 h at 50° C. The mixture is concentrated in vacuo to a yellow oily-solid (6.66 g). The crude material is chromatographed over a standard 100 g slurry-packed silica gel, eluting with 65% EtOAc/hexane. The appropriate fractions are combined and concentrated in vacuo to afford 1.30 g (82%) of methyl furo[3,2-c]pyridine-6-carboxylate as a yellow solid. MS (EI) m/z: 177 (M+).

1. stirringThe mixture is stirred for 2.5 h as the cooling bath
2. custom5.5 h
3. customat RT
4. customfinally 24 h
5. customat 50° C
6. concentrationThe mixture is concentrated in vacuo to a yellow oily-solid (6.66 g)
7. customThe crude material is chromatographed over a standard 100 g slurry-packed silica gel
8. washeluting with 65% EtOAc/hexane
9. concentrationconcentrated in vacuo