[CH:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C-]#N.[Na+].[F:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21](=[O:23])[CH3:22])=[CH:15][CH:14]=1.O>CN(C=O)C>[F:12][C:13]1[CH:14]=[CH:15][C:16]([CH:19]([CH2:20][C:21](=[O:23])[CH3:22])[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:8])=[CH:17][CH:18]=1A solution of benzaldehyde (1.650 ml, 16.32 mmol) in DMF (5 ml) was added dropwise over the course of ½ hour to a mixture of sodium cyanide (0.401 g, 8.17 mmol) in DMF (20 ml) at 35° C. Stirring was then continued for 1.5 hours at 35° C. A solution of (E)-4-(4-fluorophenyl)but-3-en-2-one (2.0 g, 12.18 mmol) and DMF (10 ml) was then slowly added dropwise over the course of 3.5 hours at 35° C. Stirring was then continued for 3.5 hours at the same temperature. The reaction mixture was treated with twice its volume of water and extracted with DCM. The combined extracts were washed with water and brine, dried with Na2SO4, filtered and concentrated to give a liquid, which was further purified by chromatography on silica gel using an automated Biotage system and EtOAc/Hex (0-50%) to give 2-(4-fluorophenyl)-1-phenylpentane-1,4-dione (1.5 g, 5.55 mmol, 45.6% yield). 1H NMR (400 MHz, CDCl3) δ (ppm) 7.95-7.93 (m, 2H), 7.50-7.46 (m, 1H), 7.40-7.32 (m, 3H), 7.26-7.21 (m, 3H), 5.11 (dd, 1H), 3.59 (dd, 1H), 2.76 (dd, 1H), 2.19 (s, 3H).
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