Benzene → HCID 23081970, compound

HRID 2238606Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14]/[CH:15]=[CH:16]/[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].CC(N=NC(C#N)(C)C)(C#N)C.C1C=CC=CC=1>>[C:18]1([CH2:17][CH2:16][CH:15]2[C:2]3[CH:3]=[C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])[CH:10]=[CH:11][C:12]=3[O:13][CH2:14]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

Reactant 3

HCID 241Benzene

HCID 6547Azobisisobutyronitrile

HCID 57445527HCID 57445527, compound

Product 1

HCID 23081970HCID 23081970, compoundYield 97.2%

Procedure

To a solution of ethyl 3-iodo-4-{[(2E)-4-phenyl-but-2-enyl]-oxy}benzoate (13.42 g, 31.73 mmol) and AIBN (0.52 g, 3.17 mmol) in benzene (900 ml) tributyltin hydride (12 ml, 44.43 mol) was added at room temperature and the reaction mixture was warmed to reflux. After 2 h, the solvent was eliminated under vacuum. The residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=95/5) affording 9.14 g of the title compound (97% yield).

Workup

temperaturethe reaction mixture was warmed to reflux
customThe residue was purified by flash chromatography on silica gel (petroleum ether/ethyl acetate=95/5)

Sources & evidence

ORD record: ord-15f04a434045465ba40ee1d6a4f26669
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07718815B2

Reaction notes

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