Iodine → HCID 15070148, compound

HRID 2081323Notes

Reaction equation

HRID 2081323 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1I)[CH3:2].C([Sn](CC[CH2:44][CH3:45])(CCCC)/C=C/[Sn](CCCC)(CCCC)CCCC)CCC.[I:46]I>>[CH2:1]([O:3][C:4](=[O:17])[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1/[CH:45]=[CH:44]/[I:46])[CH3:2]

Participants

4

Reactant 3

HCID 807IodineHCID 5378370trans-1,2-Bis(tri-n-butylstannyl)ethyleneHCID 15070116HCID 15070116, compound

Product 1

HCID 15070148HCID 15070148, compoundYield 57.5%

Procedure

Under the conditions of example 2D, 696 mg of 5-(2-iodophenoxy)-valeric acid ethyl ester and 3.2 g of (E)-1,2-bis-(tri-n-butylstannyl)-ethylene (50%) are 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. 430 mg of 5-[2-[(E)-2-iodovinyl]-phenoxy]-valeric acid ethyl ester 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-c6e25704d64f42ed9dc3e908d1af7eb6
Source dataset
uspto-grants-1993_02
Patent number
US05183925

Reaction notes

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