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

HRID 249551Notes

Reaction equation

C[CH:2]1[O:6][CH:5]([CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[C:4](=[O:18])[O:3]1.Cl>C1(C)C=CC=CC=1.C[O-].[Na+]>[OH:6][CH:5]([CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[C:4]([O:3][CH3:2])=[O:18]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of tert.-butyl 4-(2-methyl-5-oxo-1,3-dioxolan-4-yl)-3-oxobutanoate (5.16 g, 20.0 mmol) in toluene (40.0 ml), sodium methoxide (1M in methanol) (20.5 was added at 0° C. over 10 minutes in an argon atmosphere and stirred at 0° C. for 30 minutes. After dropwise adding 1N hydrochloric acid (21.0 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-methyl 6-tert.-butyl 2-hydroxy-4-oxoadipate (4.39 g, 17.83 mmol). Yield, 89.2 %.

Workup

stirringthe mixture was stirred at 0° C. for 10 minutes
customAfter evaporating off the most of the organic solvent under reduced pressure
extractionthe mixture was extracted with ethyl acetate
washwashed with a saturated saline
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-72f0804d061346248cee98979f7d08a0
Source dataset: uspto-grants-1993_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05214197

Reaction notes

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