LY88074 Trimethyl ether → 2-(4-Methoxyphenyl)-3-(4-Hydroxybenzoyl)-6-Methoxybenzo[b]thiophene

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A solution of 0.4 g (1 mmol) of [6-Methoxy-2-(4-methoxyphenyl)benzo[b]thien-3-yl][4-methoxyphenyl]methanone in 2 mL of DMF was added to a solution of 3 mL of 0.5M sodium ethanethiol in DMF. The reaction mixture was heated to 80° C. for 4 hours. The reaction mixture was allowed to cool and diluted with 10 mL of water and 10 mL of EtOAc and neutralized with 1N HCl. The reaction mixture was extracted three times with 30 mL portions of EtOAc. The combined organic extracts were washed four times with 20 mL portions of brine and dried with MgSO4 and evaporated to dryness. The crude product was chromatographed on silica eluting with 30% EtOAc in hexane, and evaporated to dryness. This yielded 0.31 g of the title compound as a yellow solid.

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