Reaktion #2035457

Reaktionsgleichung

DEAD

2-methoxy-5-hydroxypyridine

4-methoxybenzyl alcohol

PPh3

→

2-Methoxy-5-(4-methoxybenzyloxy)pyridine

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled with an ice-water bath
2. 2
   SonstigeThe resulting mixture was irradiated under microwave conditions at 90° C. for 30 minutes
3. 3
   SonstigeThe resulting reaction mixture
4. 4
   Temperaturwas cooled
5. 5
   Waschenwashed with a 1 N NaOH solution
6. 6
   Extraktionextracted with AcOEt
7. 7
   SonstigeThe organic layer was separated
8. 8
   Trocknendried (Na2SO4)
9. 9
   Sonstigethe solvent was evaporated under reduced pressure
10. 10
    SonstigeThe residue triturated with diisopropyl ether
11. 11
    SonstigeThe precipitated obtained (PPh3O)
12. 12
    Filtrationwas filtered off
13. 13
    SonstigeThe residue was purified in a manifold (vac.)

Vorschrift

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%).

Quelle