Potassium Carbonate → 4-(4-Chlorobutoxy)-7H-furo[3,2-g][1]benzopyran-7-on

HRID 225975

Reaction equation

HRID 225975 reaction equation
[CH:1]1[C:5]2=[C:6]([OH:15])[C:7]3[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:8]=3[CH:9]=[C:4]2[O:3][CH:2]=1.[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20]I.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:16][CH2:17][CH2:18][CH2:19][CH2:20][O:15][C:6]1[C:7]2[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:8]=2[CH:9]=[C:4]2[O:3][CH:2]=[CH:1][C:5]=12

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 825271-Chloro-4-iodobutaneHCID 5280371Bergaptol

Product 1

HCID 116378934-(4-Chlorobutoxy)-7H-furo[3,2-g][1]benzopyran-7-on

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

817 mg (4.041 mmol) of 5-hydroxypsoralen and 1.413 g (6.47 mmol) of 4-chlorobutyl iodide were refluxed in 80 ml of acetone in the presence of an excess of (3.0 g) anhydrous potassium carbonate for 30 hours. The progress of the reaction was monitored by thin layer chromatography. After 30 hours the reaction mixture was concentrated under reduced pressure and distilled off the solvent almost completely. 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 1×25 ml of 1% sodium hydroxide to separate trace amounts of un-reacted 5-hydroxypsoralen. The dichloromethane layer was washed with 30 ml of 2% hydrochloric acid and further washed with water to neutral pH. The dichloromethane layer was dried over anhydrous sodium sulfate and concentrated to dryness. The resulting residue was then suspended in petroleum ether and filtered to wash out the excess 4-chlorobutyl iodide. The resulting 5-(4-chlorobutoxy)psoralen was used for the synthesis of various derivatives without further purification.

Workup

  1. concentrationAfter 30 hours the reaction mixture was concentrated under reduced pressure
  2. distillationdistilled off the solvent almost completely
  3. temperatureThe oily residue was cooled
  4. additiondiluted with water
  5. extractionextracted with 3×100 ml of dichloromethane
  6. extractionThe dichloromethane layer was extracted with 1×25 ml of 1% sodium hydroxide
  7. customto separate trace amounts of un-reacted 5-hydroxypsoralen
  8. washThe dichloromethane layer was washed with 30 ml of 2% hydrochloric acid
  9. washfurther washed with water to neutral pH
  10. dry with materialThe dichloromethane layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated to dryness
  12. filtrationfiltered
  13. washto wash out the excess 4-chlorobutyl iodide
  14. customThe resulting 5-(4-chlorobutoxy)psoralen was used for the synthesis of various derivatives without further purification

Sources & evidence

ORD record
ord-c605c38a40d64af4a40522b2ba7775a1
Source dataset
uspto-grants-2009_07
Patent number
US07557138B2

Linked notes

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