Reacción #1971

Ecuación de reacción

DEAD

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

triphenyl phosphine

methanol

→

title product

Rendimiento 85.7%

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

Rendimiento 85.7%

Disolventes

THF

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowere removed under vacuum
2. 2
   Otrothe residue was purified by flash chromatography on silica gel
3. 3
   Lavadoeluting with 1:16 ethyl acetate

Procedimiento

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.

Fuente