[CH:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH2:7][S:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.N1C(C)=CC=CC=1C.FC(F)(F)C(OC(=O)C(F)(F)F)=[O:27].C([O-])(O)=O.[Na+]>C(#N)C.O>[CH:1]1[C:10]2[C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[CH:7]([OH:27])[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1
To a stirred solution of 6H-dibenzo[b,d]thiopyran-5-oxide (2 g; 0.0093 mol), 2,6-lutidine (4 ml; 0.034 mol) and acetonitrile (40 ml) was added a solution of trifluoro acetic anhydride (3.2 ml; 0.022 mol) in acetonitrile (10 ml) at 0° C. After 2 hours a solution of NaHCO3 (1 g) in water (25 ml) was quickly added at 0° C. and then the mixture was allowed to warm to room temperature. After 2 hours the mixture was poured into water (200 ml) and extracted with diethyl ether. The extracts were dried, concentrated and separated on silica gel chromatography column (ethyl acetate:cyclohexane 1:4 as eluant) to give 6H-dibenzo[b,d]thiopyran-6-ol; (1.2 g; yield 60%); m.p. 83°-86° C. By proceeding analogously the following compounds were obtained:
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