Reacción #69962

Ecuación de reacción

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

Rendimiento 84.6%

Disolventes

sodium metabisulphite

Condiciones de reacción

Tratamiento posterior

1. 1
   Otropurged with nitrogen
2. 2
   workup.ADDITIONAnhydrous acetonitrile (120 ml) is added
3. 3
   OtroThe crude reaction mixture
4. 4
   Extracciónextracted with dichloromethane (2×250 ml)
5. 5
   SecadoThe combined organics are dried over magnesium sulphate
6. 6
   Filtraciónfiltered
7. 7
   Otrothe solvent is removed under reduced pressure

Procedimiento

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)

Fuente