Dimethyl Sulfoxide → HCID 13557279, compound

Participants

Reaction Steps

Sodium acetate (53.0 g, 0.647 mole) was added to a stirred solution of N-hydroxyphthalimide (95.9 g, 0.588 mole) in dimethyl sulfoxide (600 ml) under a nitrogen atmosphere. The resulting mixture was stirred for two hours at ambient temperature, then ethyl 4-bromo-2-methyl-2-methylthiobutanoate (150.0 g, 0.588 mole) in dimethyl sulfoxide (400 ml) was added. The reaction mixture was heated at 70°-80° C. for four days. Upon cooling, the reaction mixture was poured into crushed ice and stirred. A solid precipitate was removed by filtration (50 g). The aqueous filtrate was then extracted with ether (500 ml) and methylene chloride (2×250 ml). The extracts were combined, dried and concentrated under reduced pressure to yield a brown oil. The brown oil and the solid precipitate were combined, dissolved in ethyl acetate, and washed with a 1N aqueous solution of sodium hydroxide (3×100 ml) to remove unreacted N-hydroxyphthalimide and dimethyl sulfoxide. The dried organic extract was concentrated under reduced pressure to yield a brown residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished with ethyl acetate:heptane (1:9). Appropriate fractions were combined and concentrated under reduced pressure to yield 93.0 g of ethyl 2-methyl-2-methylthio-4-(phthalimidooxy)butanoate. The NMR spectrum was consistent with the proposed structure.

Provenance & Evidence