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To a stirred solution of methyl 2-oxocyclopentanecarboxylate (4.26 g, 30 mmol) and allyl alcohol (10.2 mL, 150 mmol) in anhydrous toluene (25 mL) was added powdered zinc (0.40 g, 6 mmol). After refluxing the mixture for 48 h, it was cooled to room temperature and the suspension was filtered. The filter cake was rinsed with toluene and the combined filtrate was concentrated to afford allyl 2-oxocyclopentanecarboxylate (5.01 g, 99%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ 5.89 (ddt, J1=15.9 Hz, J2=10.5 Hz, J3=4.8 Hz, 1 H), 5.33 (dtd, J1=15.9 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 5.23 (dtd, J1=10.5 Hz, J2=2.7 Hz, J3=1.4 Hz, 1 H), 4.83-4.75 (m, 1 H), 3.18 (t, J=9.0 Hz, 1 H), 2.41-2.23 (m, 4 H), 2.22-2.07 (m, 1 H), 1.94-1.80 (m, 1 H); MS (+CI): m/z for C9H12O3: expected 168.1; found 169.1 (M+H)+.

1. temperatureAfter refluxing the mixture for 48 h
2. filtrationthe suspension was filtered
3. washThe filter cake was rinsed with toluene
4. concentrationthe combined filtrate was concentrated