Potassium Bromide → HCID 21064624, compound

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence