Potassium Bromide → HCID 21064624, compound
Reaction equation
[CH3:1][CH:2]([CH2:9][C:10]1[CH:11]=[N:12][C:13]([O:16][CH2:17][CH2:18][CH2:19][OH:20])=[CH:14][CH:15]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].CC1(C)N([O])C(C)(C)CCC1.[K+].[Br-].C([O-])(O)=O.[Na+].[O-]Cl.[Na+].S(=O)(O)[O-].[Na+]>ClCCl.C1OCCOCCOCCOCCOCCOC1.O.C1COCC1>[CH3:1][CH:2]([CH2:9][C:10]1[CH:11]=[N:12][C:13]([O:16][CH2:17][CH2:18][CH:19]=[O:20])=[CH:14][CH:15]=1)[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 0 °C
Procedure
To a solution of the product of Step 3 (0.39 g, 1.39 mmol) in dichloromethane (7 mL), and THF (2.0 mL) at 0° C., 2,2,6,6-tetramethyl-1-piperidinyloxy-radical, (TEMPO) (0.005 g), KBr (16.7 mg), NaHCO3 (0.015 g), and 18-crown-6 (0.005 g) were added. To this reaction mixture, was added dropwise a solution of NaOCl (5%, 2.5 mL) and then stirred at 0° C. for 1 hour. After stirring for 1 hour at room temperature, sodium bisulphite solution (5%, 1 mL), dichloromethane (20 mL), and water (10 mL) were added. The organic phase was washed with water (2×20 mL), dried (Na2SO4), and concentrated to dryness under reduced pressure to give ethyl β-methyl-6-(3-oxopropoxy)-3-pyridinebutanoate as a light brown liquid (0.34 g). 1H-NMR and mass spectral data were consistent with the structure. This material was used without purification in the following step.
Workup
- stirringAfter stirring for 1 hour at room temperature
- washThe organic phase was washed with water (2×20 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated to dryness under reduced pressure
Sources & evidence
- ORD record
- ord-f434a84455a84d0e8ae8c62f7e618b29
- Source dataset
- uspto-grants-2006_10
- Patent number
- US07119098B2
Reaction notes
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