反応 #155339

反応方程式

3-[5-Fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propionaldehyde

Sodium chlorite

2-methyl-2-butene

sodium dihydrogenphosphate dihydrate

→

3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propionic acid

収率 68.1%

溶媒

Water

dichloromethane

tert-butyl alcohol

water

反応条件

後処理

1. 1
   抽出the mixture was extracted with dichloromethane
2. 2
   洗浄washed with water
3. 3
   乾燥dried over anhydrous sodium sulfate
4. 4
   濃縮The dried product was concentrated under reduced pressure
5. 5
   その他The residue was purified
6. 6
   濃縮The purified product was concentrated to dryness under reduced pressure

実験手順

3-[5-Fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propionaldehyde (1.0 g, 2.61 mmol) was dissolved in water (10 ml), tert-butyl alcohol (20 ml) and dichloromethane (20 ml). Sodium chlorite (3.2 g, 35.4 mmol), 2-methyl-2-butene (19.86 gm, 283 mmol) and sodium-dihydrogenphosphate dihydrate (2 g, 2.61 mmol) were added to the resulting solution, and the solution was stirred at room temperature for 1 hour. Water was added to the reaction mixture, the mixture was extracted with dichloromethane, and then washed with water and dried over anhydrous sodium sulfate. The dried product was concentrated under reduced pressure. The residue was purified using silica gel column chromatography (dichloromethane:ethyl acetate=50:50→0:100). The purified product was concentrated to dryness under reduced pressure, giving a pale yellow powder of 3-[5-fluoro-3-(4-methoxyphenyl)-4-oxo-8-propoxy-4H-quinolin-1-yl]propionic acid (710 mg, yield: 68%).

出典