Reaction #1971

Reaction equation

DEAD

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

triphenyl phosphine

methanol

→

title product

Yield 85.7%

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

Yield 85.7%

Solvents

THF

Conditions

Workup

1. 1
   Otherwere removed under vacuum
2. 2
   Otherthe residue was purified by flash chromatography on silica gel
3. 3
   Washeluting with 1:16 ethyl acetate

Procedure

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.

Source