Water → 1-(Cyclopent-3-en-1-yl)-4-iodo-3,5-dimethyl-1H-pyrazole

HRID 2095659노트

반응식

HRID 2095659 반응식
[CH3:1][C:2]1[C:6]([I:7])=[C:5]([CH3:8])[NH:4][N:3]=1.[H-].[Na+].[CH:11]1(OS(C)(=O)=O)[CH2:15][CH:14]=[CH:13][CH2:12]1.O>CN(C=O)C>[CH:14]1([N:3]2[C:2]([CH3:1])=[C:6]([I:7])[C:5]([CH3:8])=[N:4]2)[CH2:13][CH:12]=[CH:11][CH2:15]1

참가 물질

6

반응물 4

HCID 962WaterHCID 24758Sodium hydrideHCID 971153,5-Dimethyl-4-iodo-1H-pyrazoleHCID 12174535Cyclopent-3-en-1-yl methanesulfonate

생성물 1

HCID 670043751-(Cyclopent-3-en-1-yl)-4-iodo-3,5-dimethyl-1H-pyrazole

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To an ice-cold solution of 3,5-dimethyl-4-iodo-1H-pyrazole (5.00 g, 22.5 mmol) in DMF (15 mL) was added NaH (60%, 1.08 g, 27 mmol) in portions and stirred at room temperature for 1 h. To this was added methanesulfonic acid cyclopent-3-enyl ester (4.00 g, 24.7 mmol) and heated at 60° C. overnight. The reaction mixture was poured into water and extracted with ethyl acetate (60 mL). The ethyl acetate layer was washed with brine, dried over Na2SO4, filtered and concentrated. The crude residue was purified by column chromatography using 5-10% ethyl acetate in hexane to give the title compound as an oil. 1H NMR (300 MHz, CDCl3): δ=5.75 (s, 2H), 4.97 (m, 1H), 2.79 (d, 4H, J=7.2 Hz), 2.28 (s, 3H), 2.22 (s, 3H).

후처리

  1. temperatureheated at 60° C. overnight
  2. extractionextracted with ethyl acetate (60 mL)
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by column chromatography

출처 및 근거

ORD 기록
ord-6998a22f9e984766998d572be84f0464
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445510B2

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