[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][C:10]([CH3:12])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[CH:13]1(Br)[CH2:16][CH2:15][CH2:14]1.[C:18](=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH2:18][CH:13]2[CH2:16][CH2:15][CH2:14]2)[C:10](=[O:11])[CH3:12])[CH:6]=[CH:7][CH:8]=1)#[N:2]To a solution of 1.45 g (9.07 mmol) of 1-(3-cyanophenyl)acetone in 18 mL acetonitrile, 1.1 mL (9.5 mmol) cyclobutyl bromide and 5.91 g (18.1 mmol) cesium carbonate were added. After heating the solution in a 60° C. bath overnight, it was cooled and filtered. The filtrate was partitioned between water and EtOAc and the aqueous layer was extracted with EtOAc. The combined organic layer was washed with brine, dried and concentrated. The residue was purified on a flash column using a gradient of 5-10% EtOAc/hexane to isolate the title compound. 1H NMR: (500 MHz, CDCl3): δ 1.5-2.2 (m, 9H), 2.13 (s, 3H), 3.64 (m, 1H), 7.4-7.7 (m, 4H).
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