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

HRID 55289Notes

Reaction equation

HRID 55289 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]([CH:13]=[O:14])[N:7]=1.Br[CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]/[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1>>[CH3:1][O:2][C:3](=[O:15])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:17][CH2:18][CH2:19][CH2:20]/[CH:21]=[CH:22]/[C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)=[CH:10][CH:9]=[C:8]([CH:13]=[O:14])[N:7]=1

Participants

3

Reactant 2

HCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexeneHCID 540677093-(6-Formyl-3-hydroxy-2-pyridyl)-propionic acid methyl ester

Product 1

HCID 867507683-{6-formyl-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl esterYield 29.3%

Procedure

Under the conditions of example 1 D, 510 mg of 3-(6-formyl-3-hydroxy-2-pyridyl)-propionic acid methyl ester is reacted with 730 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. 284 mg of 3-{6-formyl-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester of melting point 66°-69° C. is obtained.

Workup

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

Sources & evidence

ORD record
ord-042433b51d294964b0bff2747203ed77
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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