反应详情

According to Scheme 32 Method B: To a mixture of 2-methoxy-5-hydroxypyridine (2.87 mmol, 0.36 g), 4-methoxybenzyl alcohol (5.75 mmol, 0.72 mL) and PPh3 (5.29 mmol, 1.4 g) in THF (3.75 mL) cooled with an ice-water bath, was added dropwise DEAD (5.47 mmol, 0.86 ml). The resulting mixture was irradiated under microwave conditions at 90° C. for 30 minutes. The resulting reaction mixture was cooled, washed with a 1 N NaOH solution and extracted with AcOEt. The organic layer was separated, dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue triturated with diisopropyl ether. The precipitated obtained (PPh3O) was filtered off. The residue was purified in a manifold (vac.) using a Sep-Pak silica cartridge heptane/CH2Cl2 80/20 yielding 2-methoxy-5-(4-methoxybenzyloxy)pyridine (339 mg, 48%).

1. temperaturecooled with an ice-water bath
2. customThe resulting mixture was irradiated under microwave conditions at 90° C. for 30 minutes
3. customThe resulting reaction mixture
4. temperaturewas cooled
5. washwashed with a 1 N NaOH solution
6. extractionextracted with AcOEt
7. customThe organic layer was separated
8. dry with materialdried (Na2SO4)
9. customthe solvent was evaporated under reduced pressure
10. customThe residue triturated with diisopropyl ether
11. customThe precipitated obtained (PPh3O)
12. filtrationwas filtered off
13. customThe residue was purified in a manifold (vac.)