8-Methoxypsoralen → Xanthotoxol

HRID 22154노트

반응식

HRID 22154 반응식
[Mg].C[O:3][C:4]1[C:12]2[O:13][C:14]([CH:16]=[CH:17][C:11]=2[CH:10]=[C:6]2[CH:7]=[CH:8][O:9][C:5]=12)=[O:15]>C1C=CC=CC=1>[CH:7]1[C:6]2=[CH:10][C:11]3[CH:17]=[CH:16][C:14](=[O:15])[O:13][C:12]=3[C:4]([OH:3])=[C:5]2[O:9][CH:8]=1

참가 물질

4

반응물 2

HCID 41148-MethoxypsoralenHCID 5462224Magnesium

생성물 1

HCID 65090Xanthotoxol

시약·촉매·용매 1

HCID 241Benzene용매2회

반응 조건

온도
165 °C

실험 절차

To a suspension of magnesium (0.97 g, 0.04 mol) in dry benzene (75 ml) iodine (10.2 g, 0.04 mol) was added over a period of 1 hour. Then 75 ml of dry benzene was added and the mixture was refluxed for 1 hour. The next day, 8-methoxypsoralen (Sigma Cat. No. M 3501) (4.3 g, 0.02 mol) was added, and after stirring for 15 minutes, the solvent was evaporated under vacuum at 120° C. until the residue was practically dry. It was then further heated at 165° C. for 2 hours. The resulting solid was decomposed with dilute sulphuric acid and filtered. The solid was washed with water, suspended in dilute bisulfite solution, filtered again, washed with water and finally crystallized from dioxane and yielded colourless crystals (3.75 g), m.p. 246° C.

후처리

  1. additionwas added over a period of 1 hour
  2. temperaturethe mixture was refluxed for 1 hour
  3. additionM 3501) (4.3 g, 0.02 mol) was added
  4. customthe solvent was evaporated under vacuum at 120° C. until the residue
  5. customwas practically dry
  6. filtrationfiltered
  7. washThe solid was washed with water
  8. filtrationfiltered again
  9. washwashed with water
  10. customfinally crystallized from dioxane

출처 및 근거

ORD 기록
ord-ab8c2ceb59344aff92d6e5363ae5bf68
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05427779

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