反応 #69962

反応方程式

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

収率 84.6%

溶媒

sodium metabisulphite

反応条件

後処理

1. 1
   その他purged with nitrogen
2. 2
   workup.ADDITIONAnhydrous acetonitrile (120 ml) is added
3. 3
   その他The crude reaction mixture
4. 4
   抽出extracted with dichloromethane (2×250 ml)
5. 5
   乾燥The combined organics are dried over magnesium sulphate
6. 6
   ろ過filtered
7. 7
   その他the solvent is removed under reduced pressure

実験手順

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)

出典