Hexane → 4-tert-butyl 2,2-diethyl (4S)-1,3-dioxolane-2,2,4-tricarboxylate

Participants

Reaction Steps

6.90 g of tert-butyl (2R)-2-bromo-3-hydroxypropionate and 5.3 g of diethyl ketomalonate were mixed, and after the heat-generated reaction solution returned to room temperature, 15 ml of hexane and 6.4 g of potassium carbonate were sequentially added, followed by stirring at room temperature for 15 hours. Water was added to the reaction solution, followed by extraction with ethyl ether. The obtained organic layer was washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate. The drying agent was filtered off, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1→5/1) to obtain 8.0 g (yield: 83%) of the above identified compound as a colorless oily substance.

Provenance & Evidence