Methane → 4-(4-Phenyl-4-oxobutoxy)-7H-furo[3,2-g][1]benzopyran-7-on

HRID 225978

반응식

HRID 225978 반응식
[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.[C:16](=[O:19])([O-])[O-].[K+].[K+].[CH4:22]>CO.CC(C)=O>[C:22]1([C:16](=[O:19])[CH2:6][CH2:7][CH2:14][O:15][C:6]2[C:7]3[CH:14]=[CH:13][C:11](=[O:12])[O:10][C:8]=3[CH:9]=[C:4]3[O:3][CH:2]=[CH:1][C:5]=23)[CH:1]=[CH:5][CH:4]=[CH:9][CH:8]=1

참가 물질

5

반응물 3

HCID 297MethaneHCID 11430Potassium CarbonateHCID 5280371Bergaptol

생성물 1

HCID 577540904-(4-Phenyl-4-oxobutoxy)-7H-furo[3,2-g][1]benzopyran-7-on

시약·촉매·용매 1

HCID 21894497Aceton-methanol용매

실험 절차

497 mg (2.720 mmol) of 4-chlorobutyrophenone and 445 mg (2.968 mmol) of sodium iodide were refluxed in 30 ml acetone for 1.5 hours to obtain the iodo derivative. The reaction was monitored by TLC and also visually by the precipitation of sodium chloride. To this slurry was added 500 mg (2.473 mmol) of 5-hydroxypsoralen, an excess (2 g) of anhydrous potassium carbonate and it was refluxed for 140 hours. The progress of the reaction was monitored by thin layer chromatography. After 140 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, filtered and washed with water and dried under vacuum. The solids were suspended in 50 ml ethyl acetate and refluxed to separate the un-reacted 5-hydroxypsoralen. The ethyl acetate layer was concentrated, the resulting residue dissolved in 100 ml dichloromethane and extracted with 25 ml of 1% sodium hydroxide to separate the remaining trace amounts of un-reacted 5-hydroxypsoralen. The dichloromethane layer was washed with 30 ml of 2% hydrochloric acid solution, dried over anhydrous sodium sulfate and concentrated. The solid residue obtained was dissolved in a methanol-acetone mixture, treated with charcoal and re-crystallized from a petroleum ether-acetone (90:10) mixture.

후처리

  1. customThe reaction was monitored by TLC and also visually by the precipitation of sodium chloride
  2. concentrationAfter 140 hours the reaction mixture was concentrated under reduced pressure
  3. temperatureThe oily residue was cooled
  4. additiondiluted with water
  5. filtrationfiltered
  6. washwashed with water
  7. customdried under vacuum
  8. temperaturerefluxed
  9. customto separate the un-reacted 5-hydroxypsoralen
  10. concentrationThe ethyl acetate layer was concentrated
  11. dissolutionthe resulting residue dissolved in 100 ml dichloromethane
  12. extractionextracted with 25 ml of 1% sodium hydroxide
  13. customto separate the remaining trace amounts of un-reacted 5-hydroxypsoralen
  14. washThe dichloromethane layer was washed with 30 ml of 2% hydrochloric acid solution
  15. dry with materialdried over anhydrous sodium sulfate
  16. concentrationconcentrated
  17. customThe solid residue obtained
  18. customre-crystallized from a petroleum ether-acetone (90:10) mixture

출처 및 근거

ORD 기록
ord-70163f4ecab147f28fd4fa00ecde15b9
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557138B2

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