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

HRID 41684

Reaction equation

HRID 41684 reaction equation
[CH3:1][O:2][C:3]1[CH:11]2[CH:6]([CH:7]3[O:12][CH:10]2[CH2:9][CH2:8]3)[C:5](=[O:13])[CH:4]=1.[N+]([O-])([O-])=O.[NH4+].[Ce].[I:20]I>S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>[I:20][C:4]1[C:5](=[O:13])[CH:6]2[CH:11]([C:3]=1[O:2][CH3:1])[CH:10]1[O:12][CH:7]2[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 807IodineHCID 57418452Ammonium cerium-nitrateHCID 672834435-Methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-one

Product 1

HCID 685690024-Iodo-5-methoxy-10-oxa-tricyclo[5.2.1.0*2,6*]dec-4-en-3-oneYield 84.6%

Reagents, catalysts & solvents 1

HCID 656671Sodium PyrosulfiteSolvent

Conditions

Temperature
40 °C

Procedure

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)

Workup

  1. custompurged with nitrogen
  2. additionAnhydrous acetonitrile (120 ml) is added
  3. customThe crude reaction mixture
  4. extractionextracted with dichloromethane (2×250 ml)
  5. dry with materialThe combined organics are dried over magnesium sulphate
  6. filtrationfiltered
  7. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-6e2393f7454c4ffd9ef3a41c6f75f0c0
Source dataset
uspto-grants-2013_09
Patent number
US08530667B2

Linked notes

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