3-(1-tert-butyl-5-(4-chlorophenyl)-1H-pyrazol-3-yl)propan-1-ol → 3-(1-tert-butyl-5-(4-chlorophenyl)-1H-pyrazol-3-yl)propanal

HRID 387178Notes

Reaction equation

HRID 387178 reaction equation
[C:1]([N:5]1[C:9]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)=[CH:8][C:7]([CH2:17][CH2:18][CH2:19][OH:20])=[N:6]1)([CH3:4])([CH3:3])[CH3:2].C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[C:1]([N:5]1[C:9]([C:10]2[CH:11]=[CH:12][C:13]([Cl:16])=[CH:14][CH:15]=2)=[CH:8][C:7]([CH2:17][CH2:18][CH:19]=[O:20])=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 685612533-(1-tert-butyl-5-(4-chlorophenyl)-1H-pyrazol-3-yl)propan-1-olHCID 178418287HCID 178418287, compound

Product 1

HCID 866399213-(1-tert-butyl-5-(4-chlorophenyl)-1H-pyrazol-3-yl)propanal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1-tert-butyl-5-(4-chlorophenyl)-1H-pyrazol-3-yl)propan-1-ol (200 mg, 0.774 mmol), PCC (334 mg, 1.548 mmol), SiO2 (334 mg) was added with 5 mL of CH2Cl2 under nitrogen atmosphere and stirred for 5 hrs at room temperature. The progress and completion of the reaction were confirmed by means of TLC. Upon completion of the reaction, the reaction mixture was cooled down to room temperature and the solvent was removed from the reaction mixture under reduced pressure. The reaction mixture was diluted with EtOAc, and added with water. The aqueous layer was extracted with EtOAc and the organic layer was dried with anhydrous MgSO4 and filtered. The resulting filtrate was concentrated under reduced pressure and the resulting concentrate was passed through column chromatography (Ether:Hexane=2:3, v/v) to obtain 149 mg (75%) of target compound.

Workup

  1. customUpon completion of the reaction
  2. temperaturethe reaction mixture was cooled down to room temperature
  3. customthe solvent was removed from the reaction mixture under reduced pressure
  4. additionThe reaction mixture was diluted with EtOAc
  5. additionadded with water
  6. extractionThe aqueous layer was extracted with EtOAc
  7. dry with materialthe organic layer was dried with anhydrous MgSO4
  8. filtrationfiltered
  9. concentrationThe resulting filtrate was concentrated under reduced pressure
  10. concentrationthe resulting concentrate
  11. customHexane=2:3, v/v) to obtain 149 mg (75%) of target compound

Sources & evidence

ORD record
ord-a03108ceb63d45e29076a8f73e0eb5ba
Source dataset
uspto-grants-2013_02
Patent number
US08372844B2

Reaction notes

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