Methyl iodide → 1-(2-methoxy-2-methyl-propyl)-3-nitro-1H-pyrazole

HRID 18954

Reaction equation

HRID 18954 reaction equation
[CH3:1][C:2]([OH:13])([CH3:12])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1.[H-].[Na+].[CH3:16]I>CN(C)C=O>[CH3:16][O:13][C:2]([CH3:1])([CH3:12])[CH2:3][N:4]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[N:5]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 545944402-methyl-1-(3-nitro-1H-pyrazol-1-yl)propan-2-ol

Product 1

HCID 668993201-(2-methoxy-2-methyl-propyl)-3-nitro-1H-pyrazoleYield 88.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In a round bottom flask was placed 2-methyl-1-(3-nitro-pyrazol-1-yl)-propan-2-ol (1.39 g, 7.51 mmol) dissolved in N,N-dimethylformamide (25 mL). To this solution was added sodium hydride (667 mg, 9.01 mmol, 60% dispersion in oil) and it was stirred for 15 min until gas evolution ceased. To this was then added methyl iodide (700 μL, 11.26 mmol) and it was stirred for 2 h at 25° C. The reaction was then quenched with water (250 mL). The reaction was transferred to a separatory funnel and extracted with ethyl acetate (250 mL). The organics were dried over sodium sulfate and then concentrated with silica gel (3 g) in vacuo and purified on Biotage Flash chromatography system (40M column, silica gel, 20% ethyl acetate/hexanes) to afford 1-(2-methoxy-2-methyl-propyl)-3-nitro-1H-pyrazole (1.33 g, 88%) as a colorless oil.

Workup

  1. customIn a round bottom flask was placed
  2. customThe reaction was then quenched with water (250 mL)
  3. customThe reaction was transferred to a separatory funnel
  4. extractionextracted with ethyl acetate (250 mL)
  5. dry with materialThe organics were dried over sodium sulfate
  6. concentrationconcentrated with silica gel (3 g) in vacuo
  7. custompurified on Biotage Flash chromatography system (40M column, silica gel, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-774f2c1a831948e7a70246e8c42d989f
Source dataset
uspto-grants-2010_06
Patent number
US07741327B2

Linked notes

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