(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene → HCID 67703809, compound

HRID 55273Notes

Reaction equation

HRID 55273 reaction equation
[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[C:11]([OH:12])=[CH:10][CH:9]=[C:8]([CH2:13][CH2:14][CH:15]2[CH:20]=[CH:19][C:18](OC)=[CH:17][C:16]2=C=O)[N:7]=1.Br[CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]/[C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1>>[CH3:1][O:2][C:3](=[O:25])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:27][CH2:28][CH2:29][CH2:30]/[CH:31]=[CH:32]/[C:33]2[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=2)=[CH:10][CH:9]=[C:8]([CH2:13][CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:3]([O:2][CH3:1])=[O:25])=[CH:19][CH:20]=2)[N:7]=1

Participants

3

Reactant 2

HCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexeneHCID 86750766HCID 86750766, compound

Product 1

HCID 67703809HCID 67703809, compoundYield 106.1%

Procedure

Under the conditions of example 1 D, 280 mg of 3-{6-[2-(4-methoxy-carbonylphenyl)-ethyl]-3-hydroxy-2-pyridyl}-propionic acid methyl ester is reacted with 220 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. 230 mg of 3-{6-[2-(4-methoxycarbonylphenyl)-ethyl]-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester of melting point 59°-61° C. is obtained.

Workup

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

Sources & evidence

ORD record
ord-317b3db68004473caf8036154ef6a6fd
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

Loading…