Iodine → 2-[2-[(E)-2-iodovinyl]-phenoxy]-ethyl acetate

HRID 2081321Notes

Reaction equation

HRID 2081321 reaction equation
[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1I)(=[O:3])[CH3:2].C([Sn](CC[CH2:41][CH3:42])(CCCC)/C=C/[Sn](CCCC)(CCCC)CCCC)CCC.[I:43]I>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1/[CH:42]=[CH:41]/[I:43])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 807IodineHCID 5378370trans-1,2-Bis(tri-n-butylstannyl)ethyleneHCID 105187072-(2-Iodophenoxy)-ethyl acetate

Product 1

HCID 884678652-[2-[(E)-2-iodovinyl]-phenoxy]-ethyl acetateYield 42.2%

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

Under the conditions of example 2D, 612 mg of 2-(2-iodophenoxy)-ethyl acetate and 3.2 g of (E)-1,2-bis-(tri-n-butylstannyl)-ethylene (50%) is reacted in the presence of 47 mg of tetrakis-(triphenylphosphine)-palladium, treated with 1.02 g of iodine, worked up and chromatographed on silica gel with n-hexane/ethyl acetate=95/5. 280 mg of 2-[2-[(E)-2-iodovinyl]-phenoxy]-ethyl acetate is obtained as an oily crude product, which is used without further purification in the next stage.

Workup

  1. customchromatographed on silica gel with n-hexane/ethyl acetate=95/5

Sources & evidence

ORD record
ord-ebcb980527c3472fba6cd23f89a8d448
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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