[H-].[Na+].O[CH2:4][CH:5]=[CH:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10].[Cl:14][C:15]([Cl:19])([Cl:18])[C:16]#[N:17].C([OH:22])C>CCOCC>[Cl:14][C:15]([Cl:19])([Cl:18])[C:16]([NH:17][CH:6]([CH:5]=[CH2:4])[CH2:7][CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:22]
Sodium hydride (0.03 g of a 50% dispersion in oil, 0.5 mmol, was added to a solution of ethyl 6-hydroxy-4-hexenoate (0.7 g, 5 mmol) and trichloroacetonitrile (0.6 g, 5 mmol) in anhydrous ether (50 mL) under N2 at 0° C. After 1H, ethanol (0.5 mmol) was added and the solvent was removed in vacuo. The formation of the imidate was controled by NMR (NH, ~8.5 ppm). A solution of the crude imidate in xylene (30 mL) was heated at reflux 48H. Then the solvent was removed in vacuo and the residue was purified by flash chromatography on SiO2. (eluant AcOEt: hexane, 2:8) to give the title product (1.1 g, ~70%). 1H NMR (90 MHz) (CDCl3, TMS)δ ppm. 1.23 (t, 3H, CH3, J=6 Hz), 2.0 (t, 2H, CH2 --CH2 --CO2 , J=5 Hz), 2.36 (s, 2H, CH2CO2), 4.1 (q, 2H, CH3CH2, J=6 Hz), 4.4 (t, 1H, C---CH2, J=5 Hz), 5.1 (m, 2H, CH2), 5.76 (m, 1H, CH=CH2), 7.2 (s, 1H, NH).
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