Reacción #155343

Ecuación de reacción

O-iodoxybenzoic acid

dimethyl sulfoxide

5-fluoro-1-[2-(3-hydroxypropane-1-sulfonyl)ethyl]-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one

Water

→

3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethanesulfonyl}propionaldehyde

Rendimiento 67.0%

Disolventes

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónSubsequently, insoluble matter was filtered off
2. 2
   Otrothe filtrate was then separated
3. 3
   LavadoThe thus-obtained organic layer was washed with water
4. 4
   Concentraciónconcentrated under reduced pressure
5. 5
   OtroThe residue was purified
6. 6
   ConcentraciónThe purified material was concentrated to dryness under reduced pressure

Procedimiento

O-iodoxybenzoic acid (IBX, 1.9 g, 6.78 mmol) was added to a dimethyl sulfoxide (DMSO) solution (3 ml) of 5-fluoro-1-[2-(3-hydroxypropane-1-sulfonyl)ethyl]-3-(4-methoxyphenyl)-8-propoxy-1H-quinolin-4-one (2.7 g, 5.65 mmol) and stirred overnight at room temperature. Water and ethyl acetate were added to the reaction mixture. Subsequently, insoluble matter was filtered off, and the filtrate was then separated. The thus-obtained organic layer was washed with water and concentrated under reduced pressure. The residue was purified using silica gel column chromatography (n-hexane:ethyl acetate=2:1→0:1). The purified material was concentrated to dryness under reduced pressure, giving a white powder of 3-{2-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]ethanesulfonyl}propionaldehyde (1.8 g, yield: 67%).

Fuente