Реакция #155343

Уравнение реакции

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

Выход 67.0%

Растворители

ethyl acetate

Условия реакции

Обработка

1. 1
   ФильтрацияSubsequently, insoluble matter was filtered off
2. 2
   Другоеthe filtrate was then separated
3. 3
   ПромывкаThe thus-obtained organic layer was washed with water
4. 4
   Концентрированиеconcentrated under reduced pressure
5. 5
   ДругоеThe residue was purified
6. 6
   КонцентрированиеThe purified material was concentrated to dryness under reduced pressure

Методика

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%).

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