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

HRID 272595Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 272595
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 174Ethylene GlycolLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-0448a2383afd4b9ca650a64faa2b3d6f
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07456177B2

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