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

HRID 546178

反応式

HRID 546178 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-19ba7014e3d04cf1aa2a4e9cbcb0768a
出典データセット
uspto-grants-2011_05
特許番号
US07935699B2

関連ノート

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