Reaktion #1541098

Reaktionsgleichung

Trimethyloxonium tetrafluoroborate

3-benzyl-4-propyl-2-pyrrolidinone

sodium hydrogencarbonate

→

title compound

Ausbeute 76.2%

4-Benzyl-3-propyl-3,4-dihydro-2H-5-pyrrolyl methyl ether

Ausbeute 76.2%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextraction
2. 2
   WaschenAfter washing the organic layer with brine
3. 3
   Trocknendrying over anhydrous magnesium sulfate
4. 4
   workup.DISTILLATIONthe solvent was distilled off under reduced pressure
5. 5
   SonstigeThe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Vorschrift

Trimethyloxonium tetrafluoroborate (0.85 g, 5.7 mmol) was added to a solution of 3-benzyl-4-propyl-2-pyrrolidinone (0.83 g, 3.8 mmol) in methylene chloride (15 ml) and the mixture was stirred at room temperature for 14 hours. Saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture to render it weekly basic and then extraction was performed with ethyl acetate. After washing the organic layer with brine and drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (0.67 g) as a light yellow oil. 1H-NMR (CDCl3) δ(ppm) 0.75 (3H, t, J=7.2 Hz), 1.02-1.28 (4H, m), 2.02-2.16 (1H, m), 2.55-2.66 (1H, m), 2.69 (1H, dd, J=13.2 Hz, 8.4 Hz), 2.99 (1H, dd, J=13.2 Hz, 4.8 Hz), 3.10 (1H, dd, J=13.2 Hz, 5.2 Hz), 3.58 (1H, dd, J=13.2 Hz, 8.8 Hz), 3.83 (3H, s), 7.05-7.40 (5H, m)

Quelle