[H-].[Na+].C1(C)C=CC(S([CH2:12][N+:13]#[C-:14])(=O)=O)=CC=1.[F:16][C:17]([F:25])([F:24])/[CH:18]=[CH:19]/[C:20]([O:22][CH3:23])=[O:21].CCOCC.CS(C)=O>CCOCC.CCOC(C)=O>[F:16][C:17]([F:25])([F:24])[C:18]1[C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:12][NH:13][CH:14]=1In a round-bottomed flask was added sodium hydride (3.24 mmol, 78 mg) in Et2O (5 mL). A mixture of p-toluenesulfonylmethyl isocyanide (3.24 mmol, 634 mg) and (E)-methyl 4,4,4-trifluorobut-2-enoate (3.24 mmol, 500 mg) were added in a 2:1 mixture of Et2O/DMSO (22.5 mL). The reaction mixture was stirred for a further 30 min then quenched with H2O (10 mL) and extracted with Et2O (×3). The Et2O layers were combined and washed with brine, dried over MgSO4, filtered and the solvent removed to give a yellow/orange solid. Purification by flash chromatography (1:4 EtOAc:Hept) the desired product (154 mg, 0.80 mmol, 24.6%). 1H NMR (400 MHz, CD3OD) δ 3.79 (s, 3H) 7.20 (s, 1H) 7.50 (s, 1H).
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