[H-].[Na+].[CH2:3]([N:10]([CH2:22][CH2:23][OH:24])[C:11](=[O:21])[C:12]1[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[C:13]=1F)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CN(C=O)C>[CH2:3]([N:10]1[C:11](=[O:21])[C:12]2[CH:17]=[CH:16][C:15]([F:18])=[C:14]([F:19])[C:13]=2[O:24][CH2:23][CH2:22]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1Sodium hydride (25 mg, 0.615 mmol, 60% dispersion in mineral oil) was added slowly to a solution of N-benzyl-2,3,4-trifluoro-N-(2-hydroxyethyl)benzamide (190 mg, 0.615 mmol) in DMF (3 mL) and the pale yellow solution was stirred at RT for 16 hours. Water was added to the reaction and the mixture was subsequently extracted with DCM (4×30 mL). The combined organic phases were washed with water (3×20 mL) and saturated brine solution then dried (MgSO4), filtered and evaporated to give the desired product as a colourless oil (130 mg). 1H NMR δ (CDCl3): 3.5 (t, 2H), 4.3 (t, 2H), 4.8 (s, 2H), 6.92 (dd, 1H), 7.3-7.4 (m, 5H), 7.7 (m, 1H)
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