2,6-Lutidine → HCID 13153992, compound

Participants

Reaction Steps

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:

Provenance & Evidence