Reaction #657312

Reaction equation

2-oxopropyl methanesulfonate

3-(4-fluorophenyl)-1H-pyrazol-5-ol

potassium carbonate

→

1-{[3-(4-fluorophenyl)-1H-pyrazol-5-yl]oxy}acetone

Yield 38.1%

Solvents

ethyl acetate

DMF

Conditions

Workup

1. 1
   Temperaturethe reaction mixture was heated at 60° C. for 16 h
2. 2
   Washwashed with water (3×500 ml)
3. 3
   WashThe organic layer was washed with brine
4. 4
   Dryingdried over sodium sulphate
5. 5
   Otherevaporated under reduced pressure
6. 6
   Otherto get the crude which
7. 7
   Otherwas then purified by column chromatography with silica gel (100-200 mesh)
8. 8
   Washeluted with 10-25% ethyl acetate in hexane as eluent

Procedure

To a solution of 3-(4-fluorophenyl)-1H-pyrazol-5-ol (5 g, 28 mmol) in DMF (50 ml), potassium carbonate (7.7 g, 56 mmol) was added and the mixture was stirred for 30 min at 30° C. Thereafter, 2-oxopropyl methanesulfonate (4.7 g 30 mmol) was added drop wise and the reaction mixture was heated at 60° C. for 16 h. After completion, the crude was diluted with ethyl acetate (200 ml) and washed with water (3×500 ml). The organic layer was washed with brine, dried over sodium sulphate and evaporated under reduced pressure to get the crude which was then purified by column chromatography with silica gel (100-200 mesh) eluted with 10-25% ethyl acetate in hexane as eluent to get compound 1-{[3-(4-fluorophenyl)-1H-pyrazol-5-yl]oxy}acetone (2.5 g, yield 38%). MS (ESI): 231.0 ([M+H]+)

Source