(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene → 5-{2-(2-methoxycarbonylethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-pentanoic acid methyl ester

HRID 55312Notes

Reaction equation

HRID 55312 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[N:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11]([OH:20])=[CH:10][CH:9]=1.Br[CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]/[C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1>>[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[N:13]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH3:19])=[O:17])[C:11]([O:20][CH2:23][CH2:24][CH2:25][CH2:26]/[CH:27]=[CH:28]/[C:29]2[CH:30]=[CH:31][C:32]([O:35][CH3:36])=[CH:33][CH:34]=2)=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexeneHCID 541155615-[3-Hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-pentanoic acid methyl ester

Product 1

HCID 677037605-{2-(2-methoxycarbonylethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-pentanoic acid methyl esterYield 44.7%

Procedure

Under the conditions of example 1 D, 490 mg of 5-[3-hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-pentanoic acid methyl ester is reacted with 365 mg of (1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene, worked up, and the crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate. 293 mg of 5-{2-(2-methoxycarbonylethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-pentanoic acid methyl ester is obtained as oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-10% ethyl acetate

Sources & evidence

ORD record
ord-f4836570d78a45d2932575a1cabb3c7b
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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