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

Participants

Reaction Conditions

Reaction Steps

To a solution of tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate (16.30 g, 60.08 mmol) in toluene (120.0 ml) which had been cooled to 0° C., sodium methoxide (1M in methanol) (60.3 ml) was dropwise added in an argon atmosphere. After stirring the solution at 0° C. for 30 minutes, 1N hydrochloric acid (160.5 ml) was dropwise added and the mixture was stirred for 10 minutes at 0° C. Most of the organic solvent was evaporated off under reduced pressure, and the residual mixture was extracted with ethyl acetate and washed with a saturated saline and a phosphate buffer solution (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-methyl 6-tert.-butyl 2-hydroxy-4-oxoadipate (13.26 g, 53.85 mmol). Yield, 89.6 %.

Provenance & Evidence