Hydroxylamine → 6-Benzenesulfonyl-hexa-2,4-dienoic acid hydroxyamide

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Reaction Steps

To a solution of 6-benzenesulfonyl-hexa-2,4-dienoic acid (0.292 g, 1.15 mmol) in dry dichloromethane (5 mL) was added dropwise oxalyl chloride, at 0° C. under an atmosphere of argon. One drop on dimethylformamide was then added. After stirring at 2020 C. for one hour, a solution of aqueous hydroxylamine (50%, 0.17 mL, 2.5 mmol) in tetrahydrofuran (5 mL) was added. The mixture was stirred for an additional hour and concentrated under reduced pressure to give a yellow foam that was purified by column chromatography (8:2 ethyl acetate:40-60° C. petroleum to 100% ethyl acetate). The title compound (91 mg, 31%) was obtained as a white foam.

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