Reaction #452426

Reaction equation

2-iodopropane

2-(4-pyrazolyl)-1-ethanol

sodium carbonate

→

title compound

Yield 26.0%

2-(1-isopropyl-1H-pyrazol-4-yl)-1-ethanol

Yield 26.0%

Solvents

dimethylformamide

dimethylformamide

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was then cooled to ambient and
2. 2
   Concentrationthen concentrated under reduced pressure
3. 3
   OtherThe residue was partitioned between water and dichloromethane
4. 4
   WashThe organic phase was then washed with water
5. 5
   Dryingwas then dried over sodium sulfate
6. 6
   ConcentrationThe remaining organics were concentrated under reduced pressure

Procedure

To a solution of 1.0 gm (9.0 mMol) 2-(4-pyrazolyl)-1-ethanol in 36 mL dimethylformamide were added 2.38 gm (22.5 mMol) sodium carbonate followed by the dropwise addition of a solution of 0.89 mL (9.0 mMol) 2-iodopropane in 8 mL dimethylformamide. The reaction mixture was heated to 100° C. for 18 hours. The reaction mixture was then cooled to ambient and then concentrated under reduced pressure. The residue was partitioned between water and dichloromethane. The organic phase was then washed with water followed by saturated aqueous sodium chloride and was then dried over sodium sulfate. The remaining organics were concentrated under reduced pressure to give 0.36 gm (26.0%) of the title compound as a brown oil.

Source