1-Trityl-4-ethoxymethylpyrazole → 4-Ethoxymethylpyrazole

HRID 570075

Reaction equation

HRID 570075 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-852f47be86574ff68e08c58c5bd293f0
Source dataset
uspto-grants-2015_05
Patent number
US09023315B2

Linked notes

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