m-Chloroperbenzoic acid → 2-Benzoyloxymethyl-3-oxo-1,3-dithiolane

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Reaction Conditions

Reaction Steps

2-Benzoyloxymethyl-1,3-dithiolane (example 12) (5.2 g) was dissolved in dry methylene chloride (200 ml) and cooled to 0° C. in an ice bath. Meta-chloroperbenzoic acid (80%, 4.67 g) in methylene chloride (100 ml) was added slowly while under stirring. The mixture was stirred at room temperature for 1 hour and then poured with into saturated aqueous NaHCO3 solution (100 ml). The organic layer was separated, washed first with saturated NaHCO3 solution (2×100 ml), then with water (100 ml), and finally with brine solution (100 ml), dried over MgSO4 and filtered. The filtrate was evaporated in vacuo and the residue purified by chromatography on silica gel using ethyl acetate as eluant to give 4.0 g (74%) of pure product as a mixture cis- and trans-isomers.

Provenance & Evidence