Iodine → 4-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid ethyl ester

HRID 2081312Notes

Reaction equation

HRID 2081312 reaction equation
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1I)[CH3:2].C([Sn](CC[CH2:43][CH3:44])(CCCC)/C=C/[Sn](CCCC)(CCCC)CCCC)CCC.[I:45]I>C1(C)C=CC=CC=1.C(OCC)C.[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>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1/[CH:44]=[CH:43]/[I:45])[CH3:2]

Participants

7

Reactant 3

HCID 807IodineHCID 5378370trans-1,2-Bis(tri-n-butylstannyl)ethyleneHCID 150701154-(2-Iodophenoxy)butyric acid ethyl ester

Product 1

HCID 150701204-[2-[(E)-2-iodovinyl]-phenoxy]butyric acid ethyl ester

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 1140TolueneSolventHCID 3283Diethyl EtherSolvent2×

Procedure

1.34 g of (4-(2-iodophenoxy)-butyric acid ethyl ester and 6.4 g of (E)-1,2-bis-(tri-n-butylstannyl)-ethylene (50%) are dissolved in 12 ml of toluene, mixed with 94 mg of tetrakis-(triphenylphosphine)-palladium and heated with stirring and argon atmosphere for 2 hours to 70°-80° C. (bath temperature). After cooling to room temperature, the reaction mixture is diluted with 12 ml of diethyl ether and treated with a solution of 2.04 g of iodine in 10 ml of diethyl ether, worked up and chromatographed on silica gel with n-hexane/ethyl acetate=95/5 under the conditions of example 2C. 900 mg of 4-[-[(E)-2-iodovinyl]-phenoxy]-butyric acid ethyl ester is obtained as a yellow oil.

Workup

  1. temperatureheated
  2. customchromatographed on silica gel with n-hexane/ethyl acetate=95/5 under the conditions of example 2C

Sources & evidence

ORD record
ord-249d52b406a34fccbb90544f0eb470a8
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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