Dimethyl Sulfoxide → Methyl 8-(p-chlorophenylsulfonamido)-4-(formylmethyl)octanoate

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Reaction Steps

A solution of 0.47 ml dimethylsulfoxide in 19 ml methylene chloride is cooled to -70° and 0.41 ml oxalyl chloride is added slowly. The solution is stirred at -70° for 15 min and a solution of 0.38 g of methyl 8-(p-chlorophenylsulfonamido)-4-(2-hydroxyethyl)-octanoate (example 28) in 1 ml methylene chloride is added slowly. The solution is stirred at -60° for 15 min and 1.9 ml triethylamine is added. The mixture is allowed to warm up to room temperature, washed with saturated sodium bicarbonate solution, and the organic phase is dried, filtered and evaporated to obtain a yellow oil. This oil is taken up in ether and washed with saturated sodium bicarbonate solution. The ether layer is dried, filtered and evaporated to yield methyl 8-(p-chlorophenylsulfonamido)-4-(formylmethyl)-octanoate.

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