[F:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([O:8][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)[CH:5]=[CH:4][C:3]=1[C:9](=[O:11])[CH3:10]A solution of 1-(2-fluoro-4-hydroxy-phenyl)-ethanone (130 mmol), 3,4-dihydro-2H-pyran (260 mmol) and a catalytic amount of pyridinium p-toluenesulfonate in CH2Cl2 (200 mL) was left overnight at room temperature. The organic phase was washed with 1 N NaOH (aq) (1×50 mL) and dried (K2CO3). Evaporation in vacuo gave a brown oil, that was purified by vacuumdistillation. The desired product was isolated as clear oil in 74% yield:
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