Hydrogen Sulfide → 2-Carboxy-2-[(acetylthio)methyl]-1,2,3,4-tetrahydronaphthalene

참여 물질

반응 단계

Dissolve 2-carboxy-2-(t-butyl)thiomethyl-1,2,3,4-tetrahydronaphthalene (5.36 g, 20.0 mmol) in trifluoroacetic acid (40 mL) and add mercuric acetate (6.36 g, 20.0 mmol). Stir at ambient temperature under an atmosphere of argon for 4.5 hours, then treat with gaseous hydrogen sulfide. Remove the resulting black solid by filtration and dilute the filtrate to 100 mL with methylene chloride. Wash with water, then with brine and dry (MgSO4). Evaporate the solvent in vacuo to a residue. Mix the residue with sulfuric acid (0.3 mL of 10% solution in acetic acid) and add acetic anhydride (2.04 g, 20.0 mmol). Stir the mixture for 2 hours under an atmosphere of argon at ambient temperature, then dilute with 100 mL ethyl ether. Wash with water, brine then dry (MgSO4). Concentrate the filtrate in vacuo to give the title compound.

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