Reaction #1823165

Reaction equation

potassium hydride

(-)-2-(4-(4-hydroxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine

water

octyl p-toluenesulfonate

→

(-)-2-(4-(4-octyloxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine

Yield 56.7%

Solvents

tetrahydrofuran

toluene

Conditions

Workup

1. 1
   Otherreacted at 20°-30° C. for 2 hours
2. 2
   Washthe toluene layer was washed with water
3. 3
   Concentrationconcentrated under reduced pressure
4. 4
   OtherThe residue was purified by silica gel column chromatography

Procedure

1.1 g (2.5 mmol) of (-)-2-(4-(4-hydroxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine was dissolved in 10 ml of tetrahydrofuran. This solution was added with 0.12 g (3 mmol) of potassium hydride, stirred at 10°-20° C. for 20 minutes, further added with 0.85 g (3 mmol) of octyl p-toluenesulfonate and reacted at 20°-30° C. for 2 hours. The reaction mixture was poured into 100 ml of water and 100 ml of toluene, and the toluene layer was washed with water and concentrated under reduced pressure. The residue was purified by silica gel column chromatography using toluene/ethyl acetate as eluent to obtain 0.80 g of (-)-2-(4-(4-octyloxy-5,5,5-trifluoro-1-pentyl)phenyl)-5-decyloxypyrimidine

Source