Hydrochloric Acid → 1-Isopropyl 6-tert.-butyl 2-hydroxy-4-oxoadipate

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Reaction Conditions

Reaction Steps

In a solution of tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate (13.62 g, 50.00 mmol) in toluene (100.0 ml), the above yellow solution was dropwise added and stirred at 0° C. for 30 minutes. After dropwise adding 1N hydrochloric acid (160.0 ml), the mixture was stirred at 0° C. for 10 minutes. After evaporating off the most of the organic solvent under reduced pressure, the mixture was extracted with ethyl acetate and washed with a saturated saline and a phosphate buffer (pH 7.0). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography (hexane: acetone=2:1) to give pure 1-isopropyl 6-tert.-butyl 2-hydroxy-4-oxoadipate (11.07 g, 40.35 mmol). Yield, 80.7%.

Provenance & Evidence