Reaction #155339

Reaction equation

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

Yield 68.1%

Solvents

Water

dichloromethane

tert-butyl alcohol

water

Conditions

Workup

1. 1
   Extractionthe mixture was extracted with dichloromethane
2. 2
   Washwashed with water
3. 3
   Dryingdried over anhydrous sodium sulfate
4. 4
   ConcentrationThe dried product was concentrated under reduced pressure
5. 5
   OtherThe residue was purified
6. 6
   ConcentrationThe purified product was concentrated to dryness under reduced pressure

Procedure

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%).

Source