Ethanethiol → 2-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

Participants

Reaction Steps

2-(4-Methoxyphenyl)-3-(4-Methoxybenzoyl)-6-Methoxybenzo[b]thiophene (19.8 g, 49 mmol) was dissolved in dimethylformamide and sodium hydride (10 g of a 50% oil dispersion) was added. The reaction was cooled and ethylmercaptan (12.4 g) was added slowly. The reaction was warmed to 65° C.-70° C. until the reaction was complete. The volatiles were removed by evaporation, water was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The ethyl acetate extracts were washed with water and evaporated to dryness. The residue was chromatographed on a silica gel column eluting with 1500 mL of benzene-ethyl acetate (99:1), then benzene-ethyl acetate (97:3). The fractions containing the title compound were evaporated to dryness and the residue was crystallized from benzene to give 10.7 g of the title compound. mp 114° C.-116° C. EA calculated for C23H18O4S: C, 70.75; H, 4.64; O, 16.39. Found: C, 70.88; H, 4.50; O, 16.11.

Provenance & Evidence