[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)#[N:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:23](O)[CH2:24][OH:25].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1COCC1.[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[O:8]1[CH2:23][CH2:24][O:25][CH:7]1[C:6]1[CH:9]=[CH:10][C:3]([CH2:1][NH2:2])=[CH:4][CH:5]=1To a stirred solution of 4-cyanobenzaldehyde (1.31 g, 10.0 mmol) and 4-toluenesulfonic acid hydrate (0.19 g, 1.0 mmol) in toluene (30 mL) was added ethylene glycol (2.30 mL, 41.2 mmol). The reaction mixture was heated at reflux under Dean and Stark conditions for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with water, 10% aqueous potassium carbonate solution and brine. The organic phase was dried (magnesium sulfate), filtered and the solvent evaporated at reduced pressure. The residue was dissolved in anhydrous THF (10 mL) and added dropwise to an ice-cooled solution of lithium aluminium hydride in THF (2M in THF, 15.0 mL, 30.0 mmol). The reaction mixture was allowed to warm to room temperature at stirred at this temperature for 18 hours. Water (1.2 mL), 2M aqueous sodium hydroxide (1.2 mL) and water (3.6 mL) were added sequentially and the subsequent mixture stirred at room temperature for 30 minutes. Ethyl acetate and magnesium sulfate added and the mixture stirred for a further 30 minutes. The reaction mixture was filtered and the filtrate evaporated at reduced pressure to afford the title compound (1.56 g, 87%).
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