Reaktion #69962

Reaktionsgleichung

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

cerium ammonium nitrate

iodine

→

4-Iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Ausbeute 84.6%

Lösungsmittel

sodium metabisulphite

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigepurged with nitrogen
2. 2
   workup.ADDITIONAnhydrous acetonitrile (120 ml) is added
3. 3
   SonstigeThe crude reaction mixture
4. 4
   Extraktionextracted with dichloromethane (2×250 ml)
5. 5
   TrocknenThe combined organics are dried over magnesium sulphate
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent is removed under reduced pressure

Vorschrift

A flask is charged with 5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (3.96 g, 22 mmol), cerium ammonium nitrate (13.3 g, 24.2 mmol) and iodine (6.73 mg, 26.5 mmol) and then purged with nitrogen. Anhydrous acetonitrile (120 ml) is added, and the reaction heated to 40° C., with stirring for 2 hours. The crude reaction mixture is poured onto a saturated aqueous solution of sodium metabisulphite (250 ml) and extracted with dichloromethane (2×250 ml). The combined organics are dried over magnesium sulphate, filtered, and the solvent is removed under reduced pressure to give 4-Iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one (5.70 g)

Quelle