Sodium ethoxide → 1-(3-Methoxyphenyl)-2-(ethoxycarbonylmethyl)cyclohexene

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Combine [2-(3-methoxy-phenyl)-cyclohexylidene]-acetic acid ethyl ester (839.4 mg, 3.06 mmol), sodium ethoxide (62.5 mg, 0.92 mmol), and DMSO (6.0 mL), stir, and heat at 100° C. After 2 hours, cool to ambient temperature and extract the organic layer with ethyl acetate. Wash the ethyl acetate layer 5× with brine and dry the organic layer over sodium sulfate, and concentrate in vacuo to yield the titled compound (769.6 mg, 92%) as a clear oil. TLC Rf=0.58 in 8:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.21 (m, 1H), 6.75 (m, 3H), 4.11 (q, 2H, J=7.2 Hz), 3.79 (s, 3H), 2.91 (s, 2H), 2.28 (m, 2H), 2.12 (m, 2H), 1.72 (m, 4H), 1.24 (t, 3H, J=7.3 Hz).

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