[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:20][C:21]#N)[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1.[OH-].[K+].[CH3:25]I.O.C[N:29]([CH3:32])C=O>>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:20]([CH3:21])([CH3:25])[C:32]#[N:29])[C:6]2[O:10][C:9]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[CH:8][C:7]=2[CH:19]=1To a solution of acetonitrile 18 (0.054 g, 0.184 mmole) in 5 mL dimethylformamide was added pulverized potassium hydroxide (0.024 g, 0.390 mmole) and methyl iodide (0.0552 g, 0.0391 mmole). After stirring; at rt for 2 hours, the reaction mixture was poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 95:5) to afford 0.046 g (78%) of methyl-propionitrile 20 as a yellow solid: Mp=146–148° C., 1H NMR (DMSO-d6) δ 7.87 (d, 2 H, J=8.8 Hz), 7.26 (s, 1 H), ), 7.15 (d, 1 H, J=2.4 Hz), 7.10 (d, 2 H, J=8.9 Hz), 6.86 (d, 1 H, J=2.4 Hz), 3.82 (s, 3 H), 3.81 (s, 3 H), 1.89 (s, 6 H); MS 322 (M+H)+
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