[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([OH:9])=[CH:5][CH:4]=1.[CH2:10]([O:12][C:13](=[O:17])[C:14]#[C:15][CH3:16])[CH3:11].N12CCCN=C1CCCCC2>O1CCCC1>[CH2:10]([O:12][C:13](=[O:17])[CH:14]=[C:15]([O:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)[CH3:16])[CH3:11]A mixture of 4-methoxy-phenol (1.10 g, 8.91 mmol) and ethyl-2-butynoate (2.0 g, 17.8 mmol) in tetrahydrofuran (13.7 mL) was treated with 1,8-diazabicyclo[5.4.0]undec-7-ene (1.33 mL, 8.91 mmol). The reaction was then heated at 130° C. for 1.5 h. At this time, the reaction was cooled to 25° C. and was stirred at 25° C. overnight. At this time, the reaction was concentrated in vacuo. The residue was dissolved in dichloromethane (40 mL) and was washed with a 2N aqueous hydrochloric acid solution (1×100 mL), a 1N aqueous sodium hydroxide solution (1×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL). The organics were then dried over sodium sulfate, filtered, rinsed with dichloromethane and concentrated in vacuo. Purification by Analogix flash chromatography (40 g, 10-20% ethyl acetate/hexanes) afforded 3-(4-methoxy-phenoxy)-but-2-enoic acid ethyl ester (0.99 g, 47%) as a clear oil: HR-ES-MS m/z calculated for C13H16O4 [M+H]+ 237.1122, observed 237.1121; 1H NMR (300 MHz, DMSO-d6) δ ppm 1.11 (t, J=7.0 Hz, 3H), 2.41 (s, 3H), 3.76 (s, 3H), 3.98 (q, J=7.0 Hz, 2H), 4.63 (s, 1H), 6.99 (d, J=9.1 Hz, 2H), 7.05 (d, J=9.1 Hz, 2H).
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