Hydrochloric Acid → 1-Isopropyl 6-tert.-butyl 2-hydroxy-4-oxoadipate
Reaction equation
[CH3:1][C:2]1([CH3:19])[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>[OH:6][CH:5]([CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])[C:4]([O:3][CH:2]([CH3:19])[CH3:1])=[O:18]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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%.
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-1b201d33745d4b7dbca9e65dddb8adbb
- Source dataset
- uspto-grants-1993_05
- Patent number
- US05214197
Reaction notes
Loading…