Reaktion #1971

Reaktionsgleichung

DEAD

4-t-butoxy-2,3,6-trifluoro-5-hydroxypyridine

triphenyl phosphine

methanol

→

title product

Ausbeute 85.7%

4-t-butoxy-2,3,6-trifluoro-5-methoxypyridine

Ausbeute 85.7%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewere removed under vacuum
2. 2
   Sonstigethe residue was purified by flash chromatography on silica gel
3. 3
   Wascheneluting with 1:16 ethyl acetate

Vorschrift

To a solution of 237 mg (1.07 mmol) of 4-t-butoxy-2,3,6-trifluoro-5-hydroxypyridine, from step 275a above, in 3 mL of anhydrous THF was added 335 mg (1.277 mmol) of triphenyl phosphine and 0.060 mL (1.48 mmol) of methanol. To this solution was added 0.200 mL (1.270 mmol) of DEAD dropwise at room temperature. The reaction was complete in 10 min, so the solvents were removed under vacuum and the residue was purified by flash chromatography on silica gel, eluting with 1:16 ethyl acetate:hexane to give 215.6 mg of the title product as a colorless liquid after removal of the solvent.

Quelle