FC(F)(F)S(O/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])(=O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:24]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)#[N:25]>O1CCOCC1>[C:24]([C:26]1[CH:31]=[C:30](/[CH:7]=[CH:8]/[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:29]=[CH:28][CH:27]=1)#[N:25]To a solution of ethyl (E)-3-{[(trifluoromethyl)sulfonyl]-oxy}-2-propenoate (390 mg, 1.49 mmol) in 5 ml anhydrous dioxane was added potassium phosphate (474 mg, 2.24 mmol), 3-cyanophenyl boronic acid (217 mg, 1.49 mmol), and tetrakis (triphenylphosphine)palladium(0) (43 mg, 0.038 mmol). Reaction mixture was heated to reflux and stirred overnight. Mixture was filtered through a pad of Celite, diluted with 50 ml ethyl acetate, washed with 2×50 ml water, 2×50 ml saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo. Residue was chromatographed on silica gel using 5% EtOAc in hexane as the eluent to give ethyl (E) 3-(3-cyanophenyl)-2-propenoate (240 mg, 71%) as a clear yellow oil after drying. H1NMR (CDCl3): 1.2-1.32 (t, 3H); 2.547 (s, 3H); 4.18-4.24 (m, 2H); 6.113 (s, H); 7.47-7.725 (m, 4H). NOE confirmed stereo orientation.
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