Reaktion #471089

Reaktionsgleichung

sodium hydroxide

6-(3,5-dimethylisoxazol-4-yl)-2,2,4,4-tetramethyl-1,2,3,4-tetrahydro-furo[2,3-h]quinolin-3-one

pyridinium hydrobromide

→

title compound

Ausbeute 44.0%

8-bromo-6-(3,5-dimethylisoxazol-4-yl)-2,2,4,4-tetramethyl-1,2,3,4-tetrahydro-furo[2,3-h]quinolin-3-one

Ausbeute 44.0%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   Extraktionextracted with ethyl acetate
3. 3
   WaschenThe organic layer was washed with water and saturated brine
4. 4
   Trocknendried over sodium sulfate
5. 5
   SonstigeThe solvent was evaporated under reduced pressure
6. 6
   WaschenThe residue was subjected to normal phase chromatography (elution solvent hexane→hexane-ethyl acetate=3:2)

Vorschrift

To a solution of 6-(3,5-dimethylisoxazol-4-yl)-2,2,4,4-tetramethyl-1,2,3,4-tetrahydro-furo[2,3-h]quinolin-3-one (31 mg) obtained in Example 93, 3) in THF (1.0 ml) was added pyridinium hydrobromide perbromide (29 mg) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. The reaction solution was neutralized with 1N aqueous sodium hydroxide solution, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was subjected to normal phase chromatography (elution solvent hexane→hexane-ethyl acetate=3:2) to give the title compound (17 mg, 44%).

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