Hydrochloric Acid → HCID 19761818, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of tert.-butyl 4-(2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)-3-hydroxybutanoate (5.49 g, 20.0 mmol) in toluene (40.0 ml), sodium methoxide (1M in methanol) (30 ml) was added at 0° C. in an argon atmosphere and stirred at 0° C. for 30 minutes. After dropwise adding 1N hydrochloric acid (30.5 ml) at 0° C. over 10 minutes, the mixture was stirred at 0° C. for 10 minutes. After evaporating off the most of the organic solvent under reduced pressure, the residual mixture was extracted with ethyl acetate. The organic layer was 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-methyl 6-tert.-butyl 2,4-dihydroxyadipate (3.69 g, 14.9 mmol). Yield, 74.3 %.

Provenance & Evidence