Iodine → 5-Methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

HRID 407839

Reaktionsgleichung

Reaktionsgleichung von HRID 407839
II.[CH:3]12[O:12][CH:9]([CH2:10][CH2:11]1)[CH:8]1[CH:4]2[C:5](=[O:14])[CH2:6][C:7]1=[O:13].[CH3:15]O>>[CH3:15][O:14][C:5]1[CH:4]2[CH:8]([CH:9]3[O:12][CH:3]2[CH2:11][CH2:10]3)[C:7](=[O:13])[CH:6]=1

Komponenten

4

Edukt 3

HCID 807IodineHCID 887MethanolHCID 5935195110-Oxa-tricyclo[5.2.1.0*2,6*]decane-3,5-dione

Produkt 1

HCID 672834435-Methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Versuchsvorschrift

Iodine (0.10 g, 0.38 mmol) is added to a solution of (1RS,2SR,6RS,7SR)-10-oxa-tricyclo[5.2.1.02,6]decane-3,5-dione (2.1 g, 12.65 mmol) in methanol (50 ml) and the reaction mixture is stirred for 2 hours at room temperature. The solvent is then removed under reduced pressure, dichloromethane is added and the organic layer is washed with saturated aqueous sodium thiosulfate solution, water and brine. The organic layer is dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated under reduced pressure to give (1RS,2SR,6RS,7SR)-5-methoxy-10-oxatricyclo[5.2.1.02,6]dec-4-en-3-one and used without further purification in the next step.

Aufarbeitung

  1. customThe solvent is then removed under reduced pressure, dichloromethane
  2. additionis added
  3. washthe organic layer is washed with saturated aqueous sodium thiosulfate solution, water and brine
  4. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe filtrate is evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-28b27e2a961044e8990a77243e81ff8d
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08754242B2

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