Lawesson's reagent → HCID 18364048, compound

Participants

Reaction Steps

This reaction was performed under nitrogen and anhydrous conditions. 4,6-Dimethoxy-3-benzofuranone (1.5 g, 6.6 mmol) was dissolved in dry toluene (25 ml), and Lawesson's reagent (1.6 g, 4 mmol) was added. The mixture was refluxed with stirring for 18 hours. The mixture was cooled to room temperature and purified by chromatography with 1:1 ether:petroleum ether. Concentration of the fractions yielded yellow/orange crystals. The crystals were washed with the eluent and clean yellow crystals were produced. 1H NMR showed at least two compounds, probably the thioketone and the thiol. Yield: 400 mg (27%). NMR: δ (ppm): 3.86, 3.88, 3.94, 3.96 (OMe, 2 from thioketone and 2 from thiol), δ (ppm): 4.04 (—OCH2C(S)—), δ (ppm): 6.40 6.52 (aromatic).

Provenance & Evidence