[CH2:1]([OH:4])[CH2:2][OH:3].[C:5]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[C:11]#[N:12])(=O)[CH3:6].CC1C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:6][C:5]1([C:8]2[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=2)[C:11]#[N:12])[O:4][CH2:1][CH2:2][O:3]1To the mixture of ethylene glycol (0.22 mL, 4 mmol), 3-acetylbenzonitrile 18 (300 mg, 2.04 mmol) and benzene (10 mL) in a Dean-Stark apparatus was added a catalytic amount of p-TSA (0.1 equiv). The reaction mixture was heated at 110° C. for 4 h. The benzene was removed under reduced pressure and the residue was purified by column chromatography using ethylacetate-hexane as an eluent to give 19 (293 mg, 76%). 1H NMR (CDCl3, 400 MHz) δ 2.62 (s, 4H), 7.59 (t, J=7.6 Hz, 1H), 7.82 (d, J=7.6 Hz, 1H)), 8.15 (d, J=8 Hz, 1H), 8.21 (s, 1H).
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