8-Methoxypsoralen → Xanthotoxol

HRID 22154ノート

反応式

HRID 22154 の反応式
[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

参加物

4

反応物 2

HCID 41148-MethoxypsoralenHCID 5462224Magnesium

生成物 1

HCID 65090Xanthotoxol

試薬・触媒・溶媒 1

HCID 241Benzene溶媒2 回

反応条件

温度
165 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ab8c2ceb59344aff92d6e5363ae5bf68
出典データセット
uspto-grants-1995_06
特許番号
US05427779

反応ノート

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