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

HRID 546178

반응식

HRID 546178 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-19ba7014e3d04cf1aa2a4e9cbcb0768a
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935699B2

연결된 노트

불러오는 중…