1-Trityl-4-ethoxymethylpyrazole → 4-Ethoxymethylpyrazole

HRID 386346

Reaction equation

HRID 386346 reaction equation
C([N:20]1[CH:24]=[C:23]([CH2:25][O:26][CH2:27][CH3:28])[CH:22]=[N:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)C.CC(C)=O.Cl>[CH2:27]([O:26][CH2:25][C:23]1[CH:24]=[N:20][NH:21][CH:22]=1)[CH3:28]

Participants

4

Conditions

Temperature
80 °C

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).

Workup

  1. additionwas added to the resulting solution
  2. temperatureAfter cooling to room temperature
  3. filtrationthe reaction mixture was filtered
  4. washwashed with dichloromethane
  5. extractionextracted with dichloromethane
  6. dry with materialdried over MgSO4
  7. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-0bea6f2677724088b732e77957c79f23
Source dataset
uspto-grants-2013_02
Patent number
US08372379B2

Linked notes

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