[C:1]1([C:7](=[O:18])[C:8]#[C:9][CH2:10][O:11]C2CCCCO2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.O>CCO>[OH:11][CH2:10][C:9]#[C:8][C:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:18]To a solution of (1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-one (3.0 g, 12.3 mmol) in EtOH (20 mL) was added pyridinium p-toluenesulfonate (0.62 g, 2.5 mmol). The resulting solution was stirred for 1 h at 50° C. and then the reaction mixture was poured into water (150 mL), extracted with Et2O (3×50 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 4-hydroxy-1-phenylbut-2-yn-1-one as a dark red oil (3.2 g, crude).
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