Reaction #74607

Reaction equation

pyrazole

potassium carbonate

chloromethyl ethyl ether

→

title compound

Yield 50.0%

1-(Ethoxymethyl)-1H-pyrazole

Yield 50.0%

Solvents

acetone

Conditions

Workup

1. 1
   workup.WAITfor 2 hours at room temperature
2. 2
   FiltrationThe mixture was filtered
3. 3
   Washwashing the solid with acetone (200.0 mL)
4. 4
   ConcentrationThe filtrate was carefully concentrated in vacuo (at 400 mbar)
5. 5
   OtherThe crude material was purified by flash column chromatography
6. 6
   Washeluting with pentane:diethylether (1:1, by volume)

Procedure

To a mixture of pyrazole (10 g, 0.150 mol) and potassium carbonate (22.3 g, 0.162 mol) in acetone (200.0 mL), cooled to 0° C. under nitrogen, was added chloromethyl ethyl ether (15.0 mL, 0.162 mol) via syringe over a period of 20 minutes. The reaction was stirred for 30 minutes at 0° C. and then for 2 hours at room temperature. The mixture was filtered, washing the solid with acetone (200.0 mL). The filtrate was carefully concentrated in vacuo (at 400 mbar). The crude material was purified by flash column chromatography eluting with pentane:diethylether (1:1, by volume) to afford the title compound as a colourless oil, 9.3 g, 50% yield.

Source