Water → Tert-butyl 4-methoxy-2-oxobutanoate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

tert-Butyl 2-(2-methoxyethyl)-1,3-dithiane-2-carboxylate (1.68 g, 6.03 mmol) was dissolved in acetone (57 mL), and water (3.0 mL) was added. The flask was cooled in a cold bath at −30° C. Small aliquots of N-bromosuccinimide (10.68 g, 60 mmol) were added over 20 minutes. The reaction mixture was stirred at the same temperature for 10 minutes, and then quenched by adding an aqueous solution of sodium bicarbonate (5.05 g in 50 mL of water). Insoluble material was removed by filtration, and the solid was washed with n-hexane. To the filtrate was then added an aqueous solution of 5% sodium sulfite until the filtrate became colorless from yellow. The filtrate was diluted in water to a total volume of 250 mL, and extracted twice with n-hexane. The organic layer was washed with a saturated brine, then dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain the target compound as oil at a yield of 67%.

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