Hydrochloric Acid → 6,5'-Dimethylangelicin

HRID 1646422ノート

反応式

HRID 1646422 の反応式
[CH3:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([CH2:16][CH:17](Br)[CH2:18]Br)[C:11]=1[O:12]C(=O)C)[O:8][C:7](=[O:21])[CH:6]=[CH:5]2.[OH-].[K+].O1C2C(=CC=CC=2)C=CC1=O.[OH-].[K+].Cl>O>[CH3:18][C:17]1[O:12][C:11]2[C:10](=[C:9]3[O:8][C:7](=[O:21])[CH:6]=[CH:5][C:4]3=[CH:3][C:2]=2[CH3:1])[CH:16]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 13298924HCID 13298924、化合物HCID 131716810HCID 131716810、化合物

生成物 1

HCID 1461586,5'-Dimethylangelicin

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

To an ethanolic solution (100 ml) of 6-methyl-7-a-cetoxy-8-(2',3'-dibromopropyl) coumarin (XIII) (1.5 g) a volume of ethanolic 4% KOH solution was added, equivalent to a molar ratio coumarin/KOH 1:10. The mixture was refluxed for 80 min. in the dark, chilled, diluted with H2O (200 ml) and acidified with dil. HCl. The precipitate thus obtained was filtered, washed with H2O, dried and chromatographed on a silica gel column by eluting with CHCl3, yielding the 6,5'-dimethylangelicin (XVI), crystallized from MeOH (0.52 g; m.p. 175°-6° C.). ##STR21##

後処理

  1. temperatureThe mixture was refluxed for 80 min. in the dark,
  2. temperaturechilled
  3. customThe precipitate thus obtained
  4. filtrationwas filtered
  5. washwashed with H2O
  6. customdried
  7. customchromatographed on a silica gel column
  8. washby eluting with CHCl3

出典と根拠

ORDレコード
ord-88bed585bf4f45b5aef937feaecfc9fb
出典データセット
uspto-grants-1993_01
特許番号
US05179217

反応ノート

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