反应详情

温度

100 °C

Sodium hydride (1.02 g of a 50% suspension in mineral oil, 42 mmol) was added to a solution of 3-hydroxypyridine (2.01 g, 21 mmol) in DMF (50 ml) and the mixture stirred for 30 minutes. 2-(2-Bromoethoxy)tetrahydropyran (4.0 g, 19 mmol), (J. Am. Chem. Soc. 1948, 70, 4187), was added and the mixture heated at 100° C. for 3 hours and then stirred at ambient temperature for 18 hours. The reaction mixture was diluted with water and extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3) to give 3-(2-(tetrahydropyran-2-yloxy)ethoxy)pyridine (2.28 g, 48%).

1. stirringstirred at ambient temperature for 18 hours
2. extractionextracted with ethyl acetate
3. washThe combined extracts were washed with water
4. dry with materialdried (MgSO4)
5. customthe solvent removed by evaporation
6. customThe residue was purified by column chromatography
7. washeluting with methylene chloride/methanol mixtures (100/0 increasing to 97/3)