反应详情

温度

100 °C

2-Chloro-3-pyridinecarboxaldehyde (5.0 g, 35.0 mmol) and 4-chlorobenzenesulfinic acid sodium salt (7.75 g, 38.8 mmol) were dissolved in DMSO (120 ml) and the mixture was heated at 100° C. for 72 h under nitrogen. Upon cooling to ambient the mixture was diluted with water (500 ml) and extracted with EtOAc (3×). The combined organics were washed with water, brine, dried (MgSO4) and evaporated to dryness to afford 8.1 g of crude material. The crude compound was pre-absorbed onto silica and purified by dry pad suction column chromatography, eluting with heptane using an EtOAc gradient, to afford 4.62 g (61%) of the desired product as a white powdery solid (MP=100.5-101° C.; IR=1698 cm−1; HPLC=8.00 min>99%).

1. temperatureUpon cooling to ambient the mixture
2. extractionextracted with EtOAc (3×)
3. washThe combined organics were washed with water, brine
4. dry with materialdried (MgSO4)
5. customevaporated to dryness
6. customto afford 8.1 g of crude material
7. customThe crude compound was pre-absorbed onto silica
8. custompurified
9. customby dry pad suction column chromatography
10. washeluting with heptane using an EtOAc gradient