Isopropyl iodide → 2-(1-Isopropyl-1H-pyrazol-4-yl)ethanol

HRID 610668Notes

Reaction equation

HRID 610668 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[CH:3]=[N:2]1.C(=O)([O-])[O-].[Na+].[Na+].I[CH:16]([CH3:18])[CH3:17]>CN(C)C=O>[CH:16]([N:1]1[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[CH:3]=[N:2]1)([CH3:18])[CH3:17]

Participants

5

Conditions

Temperature
100 °C

Procedure

To a solution of 1.0 gm (9.0 mMol) 2-(4-pyrazolyl)-1-ethanol in 36 mL dimethylformamide were added 2.38 gm (22.5 mMol) sodium carbonate followed by the dropwise addition of a solution of 0.89 mL (9.0 mMol) 2-iodopropane in 8 mL dimethylformamide. The reaction mixture was heated to 100° C. for 18 hours. The reaction mixture was then cooled to ambient and then concentrated under reduced pressure. The residue was partitioned between water and dichloromethane. The organic phase was then washed with water followed by saturated aqueous sodium chloride and was then dried over sodium sulfate. The remaining organics were concentrated under reduced pressure to give 0.36 gm (26.0%) of the title compound as a brown oil.

Workup

  1. temperatureThe reaction mixture was then cooled to ambient and
  2. concentrationthen concentrated under reduced pressure
  3. customThe residue was partitioned between water and dichloromethane
  4. washThe organic phase was then washed with water
  5. dry with materialwas then dried over sodium sulfate
  6. concentrationThe remaining organics were concentrated under reduced pressure

Sources & evidence

ORD record
ord-9fe3f2ac9d9b4e3f8594bde439a1ee84
Source dataset
uspto-grants-1999_12
Patent number
US05998630

Reaction notes

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