Potassium Iodide → Pap-1

700 mg (3.462 mmol) of 5-hydroxypsoralen (crystallized) and 600 mg (3.462 mmol) of 4-phenoxybutyl bromide was refluxed in 30 ml of 2-butanone in the presence of an excess (2 g) of anhydrous potassium carbonate and catalytic amounts of potassium iodide for 24 hours. The progress of the reaction was monitored by thin layer chromatography. After 24 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 3×100 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 solid residue was dissolved in a methanol-acetone mixture, treated with charcoal and re-crystallized from a methanol-acetone (80:20) mixture.

1. concentrationAfter 24 hours the reaction mixture was concentrated under reduced pressure
2. temperatureThe oily residue was cooled
3. additiondiluted with water
4. extractionextracted with 3×100 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 solid residue was dissolved in a methanol-acetone mixture
11. additiontreated with charcoal
12. customre-crystallized from a methanol-acetone (80:20) mixture

ORDレコード

ord-0c9ecf3704c24e1da81838f2ba7f1d6d

出典データセット

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07557138B2