Reaction #657257

Reaction equation

1-trityl-4-ethoxymethylpyrazole

→

4-ethoxymethylpyrazole

Yield 44.0%

Solvents

ethanol acetone

HCl

Conditions

Workup

1. 1
   workup.ADDITIONwas added to the resulting solution
2. 2
   TemperatureAfter cooling to room temperature
3. 3
   Filtrationthe reaction mixture was filtered
4. 4
   Washwashed with dichloromethane
5. 5
   Extractionextracted with dichloromethane
6. 6
   Dryingdried over MgSO4
7. 7
   Otherthe solvent was evaporated under vacuum

Procedure

1-trityl-4-ethoxymethylpyrazole (1.800 g, 4.88 mmol) was dissolved in a mixture of ethanol/acetone (15 ml/5 ml) and 30 mL of 2N HCl was added to the resulting solution. The mixture was heated at 80° C. for 2 h. After cooling to room temperature, the reaction mixture was filtered and washed with dichloromethane. The aqueous layer was basified with 2N NaOH and extracted with dichloromethane. The organic layers were combined, dried over MgSO4 and the solvent was evaporated under vacuum yielding compound 4-ethoxymethylpyrazole as a white oil. Yield: 44% (270 mg, 2.14 mmol).

Source