Reaktion #313159

Reaktionsgleichung

5-hydroxypsoralen

4-chlorobutyronitrile

potassium carbonate

potassium iodide

→

4-(3-Cyanopropoxy)-7H-furo[3,2-g][1]benzopyran-7-on

Lösungsmittel

2-butanone

Reaktionsbedingungen

Aufarbeitung

1. 1
   EinengenAfter 48 hours the reaction mixture was concentrated under reduced pressure
2. 2
   TemperaturThe residual oily layer was cooled
3. 3
   workup.ADDITIONdiluted with water
4. 4
   Filtrationfiltered
5. 5
   WaschenThe solids were washed with water to neutral pH
6. 6
   Sonstigedried bysuction
7. 7
   Waschenfurther washed with petroleum ether
8. 8
   workup.DISSOLUTIONThe dried solids were dissolved
9. 9
   Temperaturin refluxing methanol
10. 10
    workup.ADDITIONtreated with charcoal
11. 11
    Sonstigerecrystallized from methanol

Vorschrift

800 mg (3.956 mmol) of 5-hydroxypsoralen and 0.7 ml (655.5 mg, 6.33 mmol) of 4-chlorobutyronitrile were refluxed in 50 ml of 2-butanone in the presence of an excess (2.6 g) of anhydrous potassium carbonate and catalytic amounts of potassium iodide for 48 hours. The progress of the reaction was monitored by thin layer chromatography. After 48 hours the reaction mixture was concentrated under reduced pressure. The residual oily layer was cooled, diluted with water and acidified with concentrated hydrochloric acid to pH 1. The slurry was stirred for 15-20 min and then filtered. The solids were washed with water to neutral pH, dried bysuction and then further washed with petroleum ether. The dried solids were dissolved in refluxing methanol, treated with charcoal and recrystallized from methanol.

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