Sodium Thiosulfate → Tert-butyl 4-methoxy-2-oxobutanoate

関与物質

反応手順

To a solution of tert-butyl 2-(2-methoxy-ethyl)-[1,3]dithiane-2-carboxylate (1.14 g, 4.09 mmol) in acetone (23 mL) was then added water (1.14 mL), and subsequently the solution was cooled to −15° C., to which N-bromosuccinimide (NBS, 4.37 g, 24.6 mmol) was gradually added. After stirring for 30 minutes and confirming the consumption of the starting materials by TLC, to the solution was added a solution of sodium bicarbonate (1.71 g, 20.35 mmol) in water (9.0 mL), and subsequently, an aqueous solution (8 mL) of 5% sodium thiosulfate. After extraction with dichloromethane, the organic layer was washed with water, and dried over anhydrous sodium sulfate. The organic layer was filtered and the solvent was distilled off. The resulting residue was purified with SP1 (SiO2 cartridge, 10% ethyl acetate/n-hexane, Rf=0.4) to obtain tert-butyl 4-methoxy-2-oxo-butyrate (550 mg, 72% yield).

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