Réaction #69962

Équation de réaction

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

Rendement 84.6%

Solvants

sodium metabisulphite

Conditions de réaction

Traitement

1. 1
   Autrepurged with nitrogen
2. 2
   workup.ADDITIONAnhydrous acetonitrile (120 ml) is added
3. 3
   AutreThe crude reaction mixture
4. 4
   Extractionextracted with dichloromethane (2×250 ml)
5. 5
   SéchageThe combined organics are dried over magnesium sulphate
6. 6
   Filtrationfiltered
7. 7
   Autrethe solvent is removed under reduced pressure

Mode opératoire

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)

Source