Sodium Bicarbonate → 5-methoxy-3-propyl-3,4-dihydro-2H-pyrrole

関与物質

反応手順

Trimethyloxonium tetrafluoroborate (715 mg, 4.83 mmol) was added to a solution of 4-propyl-2-pyrrolidinone (410 mg, 3.22 mmol) in methylene chloride (8 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 it was extracted with ethyl acetate. After washing the organic layer with brine and drying over anhydrous magnesium sulfate, the organic layer was subjected to distillation under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (306 mg) as a light yellow oil. 1H-NMR (CDCl3) δ(ppm) 0.90 (3H, t, J=7.2 Hz), 1.21-1.50 (4H, m), 2.13 (1H, dd, J=16.4 Hz, 16.8 Hz), 2.34-2.48 (1H, m), 2.57 (1H, dd, J=16.4 Hz, 9.2 Hz), 3.24 (1H, dd, J=13.6 Hz, 6.0 Hz), 3.71-3.90 (4H, m)

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