Reacción #313159

Ecuación de reacción

5-hydroxypsoralen

4-chlorobutyronitrile

potassium carbonate

potassium iodide

→

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

Disolventes

2-butanone

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónAfter 48 hours the reaction mixture was concentrated under reduced pressure
2. 2
   TemperaturaThe residual oily layer was cooled
3. 3
   workup.ADDITIONdiluted with water
4. 4
   Filtraciónfiltered
5. 5
   LavadoThe solids were washed with water to neutral pH
6. 6
   Otrodried bysuction
7. 7
   Lavadofurther washed with petroleum ether
8. 8
   workup.DISSOLUTIONThe dried solids were dissolved
9. 9
   Temperaturain refluxing methanol
10. 10
    workup.ADDITIONtreated with charcoal
11. 11
    Otrorecrystallized from methanol

Procedimiento

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.

Fuente