[C:1](#[N:3])[CH3:2].[H-].[Na+].[N:6]1([CH2:12][C:13]2[CH:22]=[CH:21][C:16]([C:17]([O:19]C)=O)=[CH:15][CH:14]=2)[CH2:11][CH2:10][O:9][CH2:8][CH2:7]1>O1CCCC1>[N:6]1([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([C:17](=[O:19])[CH2:2][C:1]#[N:3])=[CH:21][CH:22]=2)[CH2:7][CH2:8][O:9][CH2:10][CH2:11]1To a solution of acetonitrile (1.35 ml) in tetrahydrofuran (80 ml), cooled to 5° C., was added sodium hydride (0.94 g, 60% dispersion in oil). The mixture was stirred for 30 minutes before the addition of a solution of methyl 4-(morpholin-4-ylmethyl)benzoate (5.53 g) in tetrahydrofuran (20 ml). The resulting mixture was heated to 70° C. for 5 h. The mixture was cooled, quenched with saturated ammonium chloride (20 ml) and extracted with ethyl acetate. The organic extracts were dried (MgSO4) and evaporated to give a gum which was purified by column chromatography eluting with a 20–100% ethyl acetate/iso-hexane gradient to give 3-[4-(morpholin-4-ylmethyl)phenyl]-3-oxopropanenitrile (0.97 g).
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