Reaction #51599

Reaction equation

2,2,3,3-tetrafluoropropan-1-ol

NaH

2,6-bis-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridine

→

title compound

Yield 99.2%

2-(1-Methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxy-6-(2,2,3,3-tetrafluoropropyloxy)pyridine

Yield 99.2%

Solvents

sulfolane

pentane ethyl acetate

Conditions

Workup

1. 1
   Temperatureis cooled to ambient temperature
2. 2
   Filtrationfiltered through a bed of silica gel
3. 3
   WashThe filtrate is washed 10 times with water
4. 4
   DryingThe organic layer is dried with anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Otherevaporated in vacuo
7. 7
   OtherPurification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v)

Procedure

To a mixture of 2,2,3,3-tetrafluoropropan-1-ol (0.29 g, 2.2 mmol) in dry sulfolane (2 ml) is added NaH (60% in oil, 0.09 g, 2.2 mmol) and 2,6-bis-(1-methyl-3-trifluoromethylpyrazol-5-yloxy)-4-methoxypyridine (0.8 g, 1.8 mmol). After stirring at 110° C. for 3.7 h the mixture is cooled to ambient temperature. The resulting mixture is diluted with pentane/ethyl acetate (by volume ration 1/1) and filtered through a bed of silica gel. The filtrate is washed 10 times with water. The organic layer is dried with anhydrous magnesium sulfate, filtered and evaporated in vacuo. Purification by flash chromatography (silica gel: pentane/ethyl acetate 9/1 v/v) yields the title compound (0.72 g, 57% yield) of m.p. 73-74° C.

Source