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

HRID 2095659ノート

反応式

HRID 2095659 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6998a22f9e984766998d572be84f0464
出典データセット
uspto-grants-2013_05
特許番号
US08445510B2

反応ノート

読み込み中…