Methyl iodide → Methyl 4-iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-1-carboxylate

HRID 132997Notes

Reaction equation

HRID 132997 reaction equation
[I:1][C:2]1[C:7]2[C:8](=[O:19])[C:9]3[CH:16]=[CH:15][CH:14]=[C:13](C=O)[C:10]=3[CH2:11][CH2:12][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl[O-].[Na+].[CH3:23]I.[C:25](=[O:28])([O-])[O-:26].[K+].[K+]>CN(C)C=O.O>[I:1][C:2]1[C:7]2[C:8](=[O:19])[C:9]3[CH:16]=[CH:15][CH:14]=[CH:13][C:10]=3[CH2:11][CH2:12][C:6]=2[C:5]([C:25]([O:26][CH3:23])=[O:28])=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 23665760Sodium HypochloriteHCID 586468486-Iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-1-carboxaldehyde

Product 1

HCID 58646843Methyl 4-iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-1-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

120 mg of the mixture of 6-iodo-5-oxo-10,11-dihydro-5H-dibenzo[a,d]cycloheptene-1-carboxaldehyde and its 4-iodo form prepared in Example 6-b was oxidized by the procedure of Example 4 using sodium hypochlorite. The resulting carboxylic acids were dissolved in 10 ml of N,N-dimethylformamide, and 0.03 ml of methyl iodide and 70 mg of potassium carbonate were added, followed by stirring at room temperature for 2 hours. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified and separated by silica gel column chromatography (ethyl acetate:hexane=1:10), to give 110 mg of a mixture of the title compounds as a colorless oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated
  5. customThe residue was purified
  6. customseparated by silica gel column chromatography (ethyl acetate:hexane=1:10)

Sources & evidence

ORD record
ord-b6aa85c368104e45aa57232087716090
Source dataset
uspto-grants-2008_06
Patent number
US07390797B2

Reaction notes

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