Water → HCID 69426934, compound

HRID 1766670Notes

Reaction equation

HRID 1766670 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C:14]2[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[C:19]3[C:15]=2[CH2:16][CH2:17][CH2:18]3)=[CH:11][C:10]=1I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:30]([CH:32]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33]1)=[CH2:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(=O)([O-])[O-].[Ag+2].C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([O:13][C:14]2[C:22]([CH3:23])=[CH:21][C:20]([N+:24]([O-:26])=[O:25])=[C:19]3[C:15]=2[CH2:16][CH2:17][CH2:18]3)=[CH:11][C:10]=1[CH:31]=[CH:30][CH:32]1[CH2:36][CH2:35][C:34](=[O:37])[CH2:33]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 128393233-Ethenylcyclopentan-1-oneHCID 23031211HCID 23031211, compound

Product 1

HCID 69426934HCID 69426934, compound

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 178418647HCID 178418647, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4-(4-benzyloxy-3-iodo-phenoxy)-5-methyl-7-nitroindane (571 mg), 3-vinylcyclopentanone (197 μL), palladium acetate (II)(13 mg), triphenylphosphine (30 mg), and silver carbonate (189 mg) were stirred at 80° C. for 21 hours. To the reaction mixture were added water and ethyl acetate. The insoluble material was removed by filtration. The filtrate was extracted with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, brine successively, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1−5/1) to give the title compound (155 mg).

Workup

  1. customThe insoluble material was removed by filtration
  2. extractionThe filtrate was extracted with ethyl acetate
  3. washThe organic layer was washed with 1 mol/L hydrochloric acid, brine successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=10/1−5/1)

Sources & evidence

ORD record
ord-0789045581084cc18dcde0f65627a08e
Source dataset
uspto-grants-2007_06
Patent number
US07230031B2

Reaction notes

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