This reaction requires heating, and the quality of the sodium alkoxide must be guaranteed. The following is a patented operation. The difference is that sodium ethoxide prepared on site is used. You can refer to it.
25 g (0.213 mol) portion of phenylacetonitrile and 33 ml of ethyl acetate were added to an ethanol solution of sodium ethoxide prepared from ethanol (150 ml) and 6.38 g (0.277 mol) of metallic sodium and then heated under reflux for 3 hours. After cooling, this was concentrated under a reduced pressure, and the thus obtained residue was mixed with water and dichloromethane to separate the organic layer. This was washed with 1 N hydrochloric acid and brine and dried over magnesium sulfate , and then the solvent was evaporated. The thus obtained residue was applied to a silica gel column chromatography to obtain 3.15 g (9percent) of the title compound as a colorless oily substance from a n-hexane-ethyl acetate (5:1-- gt; 3: 1 v/v) eluate. MS (FAB)m/z: 160 (M 1) . 1H-NMR (CDCl3)δ: 2.27 (3H, s), 4.68 (1H, s), 7.36-7.52 (5H, m).