Potassium Permanganate → Furanodienone

HRID 643252ノート

反応式

HRID 643252 の反応式
[CH3:1][C@@H:2]1[C@:6]23[O:10][C@:9](O)([CH2:11][C:12](=[CH2:13])[C@@H:5]2[CH2:4][CH2:3]1)[C@H:8]([CH:15]([CH3:17])[CH3:16])[CH2:7]3.[Mn]([O-])(=O)(=O)=[O:19].[K+]>C(O)(=O)C>[CH3:16][C:15]1[C:8]2[C:7]([CH:6]=[C:2]([CH3:1])[CH2:3][CH2:4][CH:5]=[C:12]([CH3:13])[CH2:11][C:9]=2[O:10][CH:17]=1)=[O:19]

参加物

4

反応物 2

HCID 516875Potassium PermanganateHCID 14240392Curcumol

生成物 1

HCID 6442374Furanodienone収率 63%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

2.45 g (0.01 mol, 96%) of curcumol was dissolved in 40 mL of acetic acid, and to it was added an aqueous solution dissolved with 4 g potassium permanganate. The mixture was heated under reflux for several hours followed by removal of the organic solvent under vacuum. The mixture was extracted with 100 mL of 50% ethyl acetate and water. The ethyl acetate was washed with water several times and dried over anhydrous sodium sulfate. The solvent wad removed under vacuum to afford a dark solid. After separated by silica gel column, 1.45 g of white curzerenone derivative was obtained, yield: 61%, HPLC: 98%, Melting point: 138-140° C., i.e. Compound No. 31 of formula (III) wherein Z is O.

後処理

  1. additionto it was added an aqueous solution
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for several hours
  4. customfollowed by removal of the organic solvent under vacuum
  5. extractionThe mixture was extracted with 100 mL of 50% ethyl acetate and water
  6. washThe ethyl acetate was washed with water several times
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent wad removed under vacuum
  9. customto afford a dark solid
  10. customAfter separated by silica gel column

出典と根拠

ORDレコード
ord-641fe30dad61427c99e17e4f9a8d9164
出典データセット
uspto-grants-2010_04
特許番号
US07700584B2

反応ノート

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