Potassium Permanganate → 5-Methoxy-3-propyl-1-indanone

HRID 7876

Reaktionsgleichung

Reaktionsgleichung von HRID 7876
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH2:7][CH2:8][CH:9]2[CH2:12][CH2:13][CH3:14])=[CH:5][CH:4]=1.[O-:15][Mn](=O)(=O)=O.[K+]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6](=[CH:5][CH:4]=1)[C:7](=[O:15])[CH2:8][CH:9]2[CH2:12][CH2:13][CH3:14]

Komponenten

5

Edukt 2

HCID 516875Potassium PermanganateHCID 219909336-Methoxy-1-propyl-indan

Produkt 1

HCID 219908595-Methoxy-3-propyl-1-indanoneAusbeute 15,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The mixture of indans from step 2 (1.287 g, approx. 6.1 mmol) in CH2Cl2 (50 mL) was treated with a finely ground mixture of KMnO4 (7.00 g) and CuSO4.xH2O. The resulting mixture was heated at reflux for 89 hours, then cooled to room temperature and filtered through a celite pad. The filtrate was dried over MgSO4, filtered and evaporated under vacuum to an oil (1.155 g). The crude product was purified by chromatography on a Biotage FLASH 12M column, eluting with 10% EtOAc in hexanes, to afford 5-methoxy-3-propyl-1-indanone (0.188 g) as an oil. Other column fractions afforded 6-methoxy-3-propyl-1-indanone, the indan starting materials, and 5-methoxy-1-indanone.

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 89 hours
  3. filtrationfiltered through a celite pad
  4. dry with materialThe filtrate was dried over MgSO4
  5. filtrationfiltered
  6. customevaporated under vacuum to an oil (1.155 g)
  7. customThe crude product was purified by chromatography on a Biotage FLASH 12M column
  8. washeluting with 10% EtOAc in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-3f65a22cc30c4c71b7a3d15e3263d86d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087599B2

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