Hydrochloric Acid → HCID 54285185, compound

HRID 249554Notes

Reaction equation

HRID 249554 reaction equation
C[C:2]1(C)[O:6][CH:5]([CH2:7][C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4](=[O:16])[O:3]1.Cl>C1(C)C=CC=CC=1.C[O-].[Na+]>[OH:6][CH:5]([CH2:7][C:8](=[O:15])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:4]([O:3][CH3:2])=[O:16]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 19761817HCID 19761817, compound

Product 1

HCID 54285185HCID 54285185, compoundYield 84.8%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 10942334Sodium MethoxideSolvent

Procedure

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 %.

Workup

  1. stirringthe mixture was stirred at room temperature for 15 minutes
  2. customAfter evaporating off the most of the organic solvent under reduced pressure
  3. extractionthe mixture was extracted with ethyl acetate
  4. washwashed with a saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a3b7dbd6fd97436889d83a527cc76e0e
Source dataset
uspto-grants-1993_05
Patent number
US05214197

Reaction notes

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