Dimethylformamide → (E)-7-(Phenylmethoxy)-8-(3-phenyl-2-propenyl)-4H-1-benzopyran-4-one

HRID 2210073Notes

Reaction equation

HRID 2210073 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[CH:19]=[CH:18][C:12]3[C:13](=[O:17])[CH:14]=[CH:15][O:16][C:11]=3[C:10]=2[CH2:20][CH:21]=[CH2:22])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.I[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])(=O)C.[Na+].CN(C)C=O>[Cl-].C([N+](CC)(CC)CC)C.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOCC>[C:1]1([CH2:7][O:8][C:9]2[CH:19]=[CH:18][C:12]3[C:13](=[O:17])[CH:14]=[CH:15][O:16][C:11]=3[C:10]=2[CH2:20]/[CH:21]=[CH:22]/[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 11575IodobenzeneHCID 517045Sodium AcetateHCID 193799307-(phenylmethoxy)-8-(2-propenyl)-4H-1-benzopyran-4-one

Product 1

HCID 19379910(E)-7-(Phenylmethoxy)-8-(3-phenyl-2-propenyl)-4H-1-benzopyran-4-oneYield 55.5%

Reagents, catalysts & solvents 4

HCID 5946Tetraethylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 8.76 g (30 mmol) of 7-(phenylmethoxy)-8-(2-propenyl)-4H-1-benzopyran-4-one (preceding example), 6.70 g (32.84 mmol) of iodobenzene, 5.11 g (30.84 mmol) of tetraethylammonium chloride, 8.94 g (91.22 mmol) of anhydrous sodium acetate, and 64 mL of dry N,N-dimethylformamide was stirred at room temperature while being purged with a stream of argon. Palladium(II) acetate (0.38 g; 1.7 mmol) was added and stirring was continued at room temperature, for 24 hr. The dark mixture was diluted with water and worked-up with ether in the usual manner (the ether extracts were additionally washed with 12% aqueous sodium bisulfite solution). Recrystallization of the crude product from acetonitrile afforded 6.13 g (55.5%) of the title compound as a brown solid. The analytical specimen was obtained from a separate experiment as yellow crystals, mp 131°-133° C.

Workup

  1. customwhile being purged with a stream of argon
  2. stirringstirring
  3. washwere additionally washed with 12% aqueous sodium bisulfite solution)
  4. customRecrystallization of the crude product from acetonitrile

Sources & evidence

ORD record
ord-8d6403859426405ebd56ba2e5302357d
Source dataset
uspto-grants-1995_10
Patent number
US05457124

Reaction notes

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