Water → 3-(1H-pyrazol-1-yl)cyclopentan-1-one

HRID 655148Notes

Reaction equation

HRID 655148 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.[C:6]1(=[O:11])[CH2:10][CH2:9][CH:8]=[CH:7]1.O>C(Cl)Cl>[N:1]1([CH:8]2[CH2:9][CH2:10][C:6](=[O:11])[CH2:7]2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 1048PyrazoleHCID 135882-Cyclopenten-1-one

Product 1

HCID 594861173-(1H-pyrazol-1-yl)cyclopentan-1-oneYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of pyrazole (6.85 g, 100 mmol), 2-cyclopenten-1-one (19.3 g, 235 mmol) and ScCl3 (1.42 g, 9.38 mmol) in anhydrous CH2Cl2 (3 mL) was stirred at room temperature for 30 min. The reaction mixture was poured into water and then extracted with CH2Cl2. The organic layer was washed with brine, and dried over anhyd Na2SO4 followed by the removal of solvent. The crude product was purified by column chromatography (Hexane/EtOAc=4/1) to yield 3-(1H-pyrazol-1-yl)cyclopentan-1-one (14.1 g, 94%) as yellow oil.

Workup

  1. extractionextracted with CH2Cl2
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhyd Na2SO4
  4. customfollowed by the removal of solvent
  5. customThe crude product was purified by column chromatography (Hexane/EtOAc=4/1)

Sources & evidence

ORD record
ord-72aeea3eb72b481cbdfed452a98fae21
Source dataset
uspto-grants-2011_12
Patent number
US08071591B2

Reaction notes

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