Acetic Acid → HCID 19347983, compound

Participants

Reaction Conditions

Reaction Steps

Hydrogen peroxide in water (0.23 ml of 30% w/v, 2.05 mmol) was added to a mixture of ethyl 3-[2-(hydroxymethyl)phenylsulfanyl]-6-(3-pyridylmethoxy)benzo[b]thiophene-2-carboxylate (Example 13, 770 mg, 1.71 mmol) in acetic acid (5 ml), and 2M aqueous hydrochloric acid (0.8 ml). The mixture was heated to 100° C. for 3 hours, cooled, and the solvents removed under reduced pressure. The residue was partitioned between ethyl acetate and aqueous sodium bicarbonate solution, and the organic layer was separated, dried (magnesium sulfate) and concentrated under vacuo. The residue was flash chromatographed on silica gel using a mixture of 75% ethyl acetate and 25% hexane as eluant, to give the title compound as a colourless solid (500 mg).

Provenance & Evidence