Ethyl Acetate → (4S, 4aR, 6R)-6-Acetyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one

HRID 1006308

Reaktionsgleichung

Reaktionsgleichung von HRID 1006308
[CH3:1][C@H:2]1[C@:8]2([CH3:16])[CH2:9][C@H:10]([C:13](C)=[CH2:14])[CH2:11][CH2:12][C:7]2=[CH:6][C:4](=[O:5])[CH2:3]1.[OH:17]OS([O-])=O.[K+].[O-]S([O-])=O.[Na+].[Na+].CCOC(C)=O>CN(C=O)C.O=[Os](=O)(=O)=O>[C:13]([C@@H:10]1[CH2:11][CH2:12][C:7]2[C@@:8]([CH3:16])([C@@H:2]([CH3:1])[CH2:3][C:4](=[O:5])[CH:6]=2)[CH2:9]1)(=[O:17])[CH3:14]

Komponenten

7

Edukt 4

HCID 8857Ethyl AcetateHCID 24437Sodium SulfiteHCID 1268142(+)-NootkatoneHCID 23707502Potassium hydroxy sulfite

Produkt 1

HCID 69919115(4S, 4aR, 6R)-6-Acetyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 30318Osmium TetroxideKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Nootkatone (250 mg) was dissolved in DMF (15 mL), and OsO4 (0.14 mL, 2.5% in tBuOH) was added and stirred for 5 min. OXONE (1.40 g) was added in one portion and the reaction had a final volume (18 mL). The reaction was stirred at room temperature for 3 hours or until the solution becomes colorless. This usually marks the completion of the reaction which was verified by TLC or GC. Na2SO3 (3.0 g) was added, to reduce the remaining Os(VIII), and stirred for an additional hour or until solution became dark brown/black. EtOAc was added to extract the products and 1N HCl was used to dissolve the salts. The organic extract was washed with 1N HCl (100 mL×3) and brine (100 mL), dried over Na2SO4, and the solvent was removed under reduced pressure to obtain the crude product. (4S, 4aR, 6R)-6-Acetyl-4,4a-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one was obtained in 60% yield after purification by silica gel column chromatography.

Aufarbeitung

  1. stirringThe reaction was stirred at room temperature for 3 hours or until the solution
  2. customthe completion of the reaction which
  3. stirringstirred for an additional hour or until solution
  4. extractionto extract the products and 1N HCl
  5. dissolutionto dissolve the salts
  6. extractionThe organic extract
  7. washwas washed with 1N HCl (100 mL×3) and brine (100 mL)
  8. dry with materialdried over Na2SO4
  9. customthe solvent was removed under reduced pressure
  10. customto obtain the crude product

Quellen und Nachweise

ORD-Eintrag
ord-0be4f6fe76994d19a55261015af85dca
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787671B2

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