Acetone → (1R*,5S*)-3,4-dichloro-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one

HRID 1470851Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1470851
[Cl:1][C:2]1[C@:3]2([CH3:13])[O:12][C@H:6]([C:7](Cl)(Cl)[C:8]=1[Cl:9])[CH:5]=[CH:4]2.CC(C)=[O:16].C(=O)(O)[O-].[Na+]>[N+]([O-])([O-])=O.[Ag+].O>[Cl:9][C:8]1[C:7](=[O:16])[C@@H:6]2[O:12][C@:3]([CH3:13])([C:2]=1[Cl:1])[CH:4]=[CH:5]2

Komponenten

6

Edukt 3

HCID 180AcetoneHCID 516892Sodium BicarbonateHCID 67533581(1R*,5S*)-2,3,4,4-tetrachloro-1-methyl-8-oxabicyclo[3.2.1]octa-2,6-diene

Produkt 1

HCID 67533525(1R*,5S*)-3,4-dichloro-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24470Silver NitrateKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Silver nitrate (166 g, 0.982 mol) is added to a stirred mixture of (1R*,5S*)-2,3,4,4-tetrachloro-1-methyl-8-oxabicyclo[3.2.1]octa-2,6-diene (83 g, 0.491 mol), acetone (1500 ml) and water (1500 ml) and the mixture is heated at 65° C. for 16 hours. The reaction mixture is cooled to room temperature, and a saturated solution of aqueous sodium bicarbonate is added to adjust the pH to 7-8. The mixture is filtered through a plug of diatomaceous earth, and the filtrate is concentrated in vacuo to remove most of the acetone. The aqueous mixture is extracted with ethyl acetate (3×500 ml) and the organic extracts are combined, dried over anhydrous sodium sulfate, filtered and the filtrate is evaporated. The residue is purified by flash column chromatography on silica gel to give (1R*,5S*)-3,4-dichloro-5-methyl-8-oxabicyclo[3.2.1]octa-3,6-dien-2-one (29.5 g) as a yellow oil.

Aufarbeitung

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationThe mixture is filtered through a plug of diatomaceous earth
  3. concentrationthe filtrate is concentrated in vacuo
  4. customto remove most of the acetone
  5. extractionThe aqueous mixture is extracted with ethyl acetate (3×500 ml)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customthe filtrate is evaporated
  9. customThe residue is purified by flash column chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-3fa1c5cd27a344cfa780261e6779beef
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09006429B2

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