Réaction #45739

Équation de réaction

2-Cyclopropyl-7-fluoro-5-methyl-6-vinyl-1,3-benzoxazole

sodium sulfite

2,6-lutidine

sodium metaperiodate

→

compound

Rendement 86.0%

2-Cyclopropyl-7-fluoro-6-formyl-5-methyl-1,3-benzoxazole-4-carbonitrile

Rendement 86.0%

Solvants

ethyl acetate

1,4-dioxane

water

water

brine

Conditions de réaction

Traitement

1. 1
   ExtractionThe aqueous layer was further extracted twice with ethyl acetate
2. 2
   Lavagewashed with saturated brine
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   AutreThe insoluble matter was separated by filtration
5. 5
   Autrethe solvent was evaporated away under reduced pressure
6. 6
   Autrethe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=6:1)

Mode opératoire

2-Cyclopropyl-7-fluoro-5-methyl-6-vinyl-1,3-benzoxazole-4-(carbonitrile (I-180) (500 mg, 2.06 mmol) was dissolved in 1,4-dioxane (7.5 ml) and water (2.5 ml), then at room temperature, 2,6-lutidine (481 μl, 4.13 mmol), a catalytic amount of osmium tetroxide and sodium metaperiodate (1.766 g, 8.26 mmol) were added. After stirring at the same temperature for 13 hours, sodium sulfite (purity 90%, 1.61 g, 12.38 mmol) and water (5 ml) were added. The solution was fractionated with ethyl acetate and saturated brine. The aqueous layer was further extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away under reduced pressure, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=6:1) to obtain the entitled compound (435 mg, 86%) as a white solid.

Source