Water → 3-[(Cyclopent-3-en-1-yl)methyl]-2-methoxypyridine

HRID 272595ノート

反応式

HRID 272595 の反応式
[CH:1]1([C:6]([C:8]2[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=2)=O)[CH2:5][CH:4]=[CH:3][CH2:2]1.O.NN.[OH-].[K+].O>C(O)CO>[CH:1]1([CH2:6][C:8]2[C:9]([O:14][CH3:15])=[N:10][CH:11]=[CH:12][CH:13]=2)[CH2:2][CH:3]=[CH:4][CH2:5]1

参加物

6

反応物 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 59837860(Cyclopent-3-en-1-yl)(2-methoxypyridin-3-yl)methanone

生成物 1

HCID 598378653-[(Cyclopent-3-en-1-yl)methyl]-2-methoxypyridine収率 51%

試薬・触媒・溶媒 1

HCID 174Ethylene Glycol溶媒

実験手順

Cyclopent-3-enyl-(2-methoxy-pyridin-3-yl)-methanone (10.0 g, 49.3 mmol), hydrazine hydrate (6.33 g, 198 mmol) and pulverized potassium hydroxide (85% KOH) (16.8 g, 300 mmol) were warmed in ethylene glycol (100 mL) until solution occurred at 100° C. then to 180° C. for 18 h. The mixture was cooled to room temperature and treated with water (100 mL) then extracted with 50% EtOAc/hexanes (3×80 mL). The organic layer was washed with saturated aqueous NaCl solution, dried over Na2SO4 and concentrated to an oil. Purification by chromatography on silica gel eluting with 10% EtOAc/hexanes provided the desired product as an oil 4.75 g (51%). (TLC 10% Et2O/hexanes Rf 0.80); 1H NMR (400 MHz, CDCl3) δ 8.01 (dd, J=5.0, 1.7 Hz, 1H), 7.37 (dd, J=7.2, 1.5 Hz, 1H), 6.81 (dd, J=7.2, 5.0 Hz, 1H), 5.66 (s, 2H), 3.95 (s, 3H), 2.61 (m, 3H), 2.40 (m, 2H), 2.03 (m, 2H); GCMS m/z 189 (M)+. 3-Cyclopent-3-enyl-1H-pyrazolo[3,4-b]pyridine was also isolated 4.45 g (49%).

後処理

  1. customoccurred at 100° C.
  2. extractionthen extracted with 50% EtOAc/hexanes (3×80 mL)
  3. washThe organic layer was washed with saturated aqueous NaCl solution
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated to an oil
  6. customPurification by chromatography on silica gel eluting with 10% EtOAc/hexanes

出典と根拠

ORDレコード
ord-0448a2383afd4b9ca650a64faa2b3d6f
出典データセット
uspto-grants-2008_11
特許番号
US07456177B2

反応ノート

読み込み中…