Water → 1-(Cyclopent-3-en-1-yl)-4-iodo-3,5-dimethyl-1H-pyrazole

HRID 2095659Notes

Reaction equation

HRID 2095659 reaction equation
[CH3:1][C:2]1[C:6]([I:7])=[C:5]([CH3:8])[NH:4][N:3]=1.[H-].[Na+].[CH:11]1(OS(C)(=O)=O)[CH2:15][CH:14]=[CH:13][CH2:12]1.O>CN(C=O)C>[CH:14]1([N:3]2[C:2]([CH3:1])=[C:6]([I:7])[C:5]([CH3:8])=[N:4]2)[CH2:13][CH:12]=[CH:11][CH2:15]1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 971153,5-Dimethyl-4-iodo-1H-pyrazoleHCID 12174535HCID 12174535, compound

Product 1

HCID 670043751-(Cyclopent-3-en-1-yl)-4-iodo-3,5-dimethyl-1H-pyrazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice-cold solution of 3,5-dimethyl-4-iodo-1H-pyrazole (5.00 g, 22.5 mmol) in DMF (15 mL) was added NaH (60%, 1.08 g, 27 mmol) in portions and stirred at room temperature for 1 h. To this was added methanesulfonic acid cyclopent-3-enyl ester (4.00 g, 24.7 mmol) and heated at 60° C. overnight. The reaction mixture was poured into water and extracted with ethyl acetate (60 mL). The ethyl acetate layer was washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by column chromatography using 5-10% ethyl acetate in hexane to give the title compound as an oil. 1H NMR (300 MHz, CDCl3): δ=5.75 (s, 2H), 4.97 (m, 1H), 2.79 (d, 4H, J=7.2 Hz), 2.28 (s, 3H), 2.22 (s, 3H).

Workup

  1. temperatureheated at 60° C. overnight
  2. extractionextracted with ethyl acetate (60 mL)
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by column chromatography

Sources & evidence

ORD record
ord-6998a22f9e984766998d572be84f0464
Source dataset
uspto-grants-2013_05
Patent number
US08445510B2

Reaction notes

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