Potassium Iodide → 4-(3-Phenoxypropoxy)-7H-furo(3,2-g)(1)benzopyran-7-one

HRID 563126Notes

Reaction equation

HRID 563126 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.[O:16]([CH2:23][CH2:24][CH2:25]Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(=O)CC>[O:16]([CH2:23][CH2:24][CH2:25][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)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 68522Benzene, (3-bromopropoxy)-HCID 5280371Bergaptol

Product 1

HCID 115517614-(3-Phenoxypropoxy)-7H-furo(3,2-g)(1)benzopyran-7-one

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-bf23179b39a545f3b32a6f1d57c66a31
Source dataset
uspto-grants-2011_11
Patent number
US08067460B2

Reaction notes

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