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

HRID 546178

Reaktionsgleichung

Reaktionsgleichung von HRID 546178
[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

Komponenten

5

Edukt 3

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

Produkt 1

HCID 668993201-(2-methoxy-2-methyl-propyl)-3-nitro-1H-pyrazoleAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a round neck flask was placed 2-methyl-1-(3-nitro-pyrazol-1-yl)-propan-2-ol (Example 74, 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.

Aufarbeitung

  1. customIn a round neck 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)

Quellen und Nachweise

ORD-Eintrag
ord-19ba7014e3d04cf1aa2a4e9cbcb0768a
Quelldatensatz
uspto-grants-2011_05
Patentnummer
US07935699B2

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