Water → 2-(1-Methyl-1H-pyrazol-4-yl)ethanol

HRID 385887Notes

Reaction equation

HRID 385887 reaction equation
[NH:1]1[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[CH:3]=[N:2]1.[OH-].[K+].[CH3:11]I.O>C(O)C>[CH3:11][N:1]1[CH:5]=[C:4]([CH2:6][CH2:7][OH:8])[CH:3]=[N:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 42936042-(1H-Pyrazol-4-yl)ethanol

Product 1

HCID 170280762-(1-Methyl-1H-pyrazol-4-yl)ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution cooled (0° C.) of 2-(1H-pyrazol-4-yl)ethanol (93 g, 0.83 mol) and potassium hydroxide (48.8 g, 0.87 mol) in absolute ethanol (9.25 L) was added methyl iodide (178 g, 1.25 mol) dropwise. The mixture was allowed to react for 30 min, at which time it was poured into water (400 mL) and extracted with diethyl ether (4×100 mL). The combined organic layers were dried (Na2SO4), filtered, concentrated in vacuo, and purified by vacuum distillation to afford the title compound.

Workup

  1. customto react for 30 min, at which time it
  2. extractionextracted with diethyl ether (4×100 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. distillationpurified by vacuum distillation

Sources & evidence

ORD record
ord-925e031597ef44eda47f838e3ea4011f
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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