Ethanethiol → 5-[Bis(ethylsulfanyl)methylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione

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Reaction Steps

A solution of 5-[bis(methylthio)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione (2.3 g, 9.2 mmole, described in example 3), ethanethiol (8.4 g, 10 mL, 135 mmole) and sodium methoxide (480 mg, 20.7 mmole) in dry methanol (12 mL) was stirred at 20°-22° C. for 30 min. The solution was poured into ice water. The resultant mixture was extracted with ethyl acetate. The combined extracts were washed with water, dried (MgSO4) and concentrated to dryness under reduced pressure. The residue was purified by HPLC (20% ethyl acetate in hexane, v/v). The purest fractions were combined. The solvent was removed under reduced pressure to give 0.59 g of the title compound as an oil; NMR (CDCl3) δ 1.36 (t, J=7 Hz, 6H), 1.72 (s, 6H), 3.11 (3t, J=7 Hz, 4H); IR (CHCl3) 1715 cm-1 ; UVλmax (MeOH) 345 nm (ε 13,040), 215 (8160).

Provenance & Evidence