Hydrochloric Acid → HCID 54285185, compound

Participants

Reaction Steps

To a solution of ethyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate (480 mg, 1.97 mmol) in toluene (2.0 ml), sodium methoxide (1M in methanol) (2.1 ml) was dropwise added at 0° C. in an argon atmosphere and stirred for 30 minutes. To the mixture, 1N hydrochloric acid (2.1 ml) was dropwise added and the mixture was stirred at room temperature for 15 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:ethyl acetate=5:1) to give pure 1-methyl 6-ethyl 2-hydroxy-4-oxoadipate (366 mg, 1.67 mmol). Yield, 85 %.

Provenance & Evidence