反应详情

700 mg (3.5 mmol) of 5-hydroxypsoralen and 750 mg (3.5 mmol) of 3-phenoxypropyl bromide were refluxed in 30 ml of 2-butanone in the presence of an excess of anhydrous potassium carbonate (3.0 g) and catalytic amounts of potassium iodide for 36 hours. The progress of the reaction was monitored by thin layer chromatography. After 36 hours the reaction mixture was concentrated under reduced pressure. The oily residue was cooled and diluted with water. The aqueous solution was then acidified with concentrated hydrochloric acid to pH 1. The slurry was stirred for 15-20 min and extracted with 3×30 ml of dichloromethane. The dichloromethane layer was extracted with 25 ml of 1% sodium hydroxide to separate the un-reacted 5-hydroxypsoralen. The dichloromethane layer was washed with 30 ml of 2% hydrochloric acid, dried over anhydrous sodium sulfate and concentrated. The resulting oily residue was dissolved in methanol, treated with charcoal and re-crystallized from a methanol-ethyl acetate (10:90) mixture.

1. concentrationAfter 36 hours the reaction mixture was concentrated under reduced pressure
2. temperatureThe oily residue was cooled
3. additiondiluted with water
4. extractionextracted with 3×30 ml of dichloromethane
5. extractionThe dichloromethane layer was extracted with 25 ml of 1% sodium hydroxide
6. customto separate the un-reacted 5-hydroxypsoralen
7. washThe dichloromethane layer was washed with 30 ml of 2% hydrochloric acid
8. dry with materialdried over anhydrous sodium sulfate
9. concentrationconcentrated
10. dissolutionThe resulting oily residue was dissolved in methanol
11. additiontreated with charcoal
12. customre-crystallized from a methanol-ethyl acetate (10:90) mixture