C[O:2][C:3](=O)[CH:4]=[CH2:5].[F:7][C:8]1[CH:13]=[CH:12][C:11]([CH2:14][C:15]#[N:16])=[CH:10][CH:9]=1.C[O-:18].[Na+].Cl.[CH2:21]1[CH2:25][O:24][CH2:23][CH2:22]1>CO>[CH3:23][O:24][C:25]([CH:21]1[CH2:22][C:14]([C:15]#[N:16])([C:11]2[CH:12]=[CH:13][C:8]([F:7])=[CH:9][CH:10]=2)[CH2:5][CH2:4][C:3]1=[O:2])=[O:18]
70 mL of methylacrylate and 50 g of 4-fluorophenylacetonitrile were dissolved in a mixture of 200 mL of THF and 50 mL of dry methanol. 150 mL of sodium methylate (30% in methanol) were added dropwise, while temperature was maintained below 40° C. The mixture was stirred at room temperature for 15 h and heated for another 4 h at 50° C. When the reaction was complete, the mixture was allowed to cool to room temperature and poured onto a cold 2N aqueous hydrochloric acid solution. The aqueous layer was extracted three times with ethyl acetate and the combined organic layer was washed with water and brine, dried over magnesium sulphate and evaporated to give 101.5 g of the desired product. Rt=1.59 min (Method 5). Detected mass: 276.2 (M+H+).
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