반응 #69962

반응 방정식

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

수율 84.6%

용매

sodium metabisulphite

반응 조건

후처리

1. 1
   기타purged with nitrogen
2. 2
   workup.ADDITIONAnhydrous acetonitrile (120 ml) is added
3. 3
   기타The crude reaction mixture
4. 4
   추출extracted with dichloromethane (2×250 ml)
5. 5
   건조The combined organics are dried over magnesium sulphate
6. 6
   여과filtered
7. 7
   기타the solvent is removed under reduced pressure

실험 절차

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)

출처