Phenylacetylene → 3-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-(2-phenylethinyl)-2-pyridyl}-propionic acid methyl ester

HRID 55272Notes

Reaction equation

HRID 55272 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][CH:9]=[C:8](I)[N:7]=1.[C:29]1([C:35]#[CH:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][C:6]1[C:11]([O:12][CH2:13][CH2:14][CH2:15][CH2:16]/[CH:17]=[CH:18]/[C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)=[CH:10][CH:9]=[C:8]([C:36]#[C:35][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[N:7]=1

Participants

3

Reactant 2

HCID 10821PhenylacetyleneHCID 867507633-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester

Product 1

HCID 677037263-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-(2-phenylethinyl)-2-pyridyl}-propionic acid methyl esterYield 56.5%

Procedure

Under the conditions of example 5 A, 500 mg of 3-{6-iodo-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid methyl ester is reacted with 102 mg of phenylacetylene, worked up, and the crude product is chromatographed on silica gel with hexane/0-7% ethyl acetate. 265 mg of 3-{3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-(2-phenylethinyl)-2-pyridyl}-propionic acid methyl ester is obtained as oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-7% ethyl acetate

Sources & evidence

ORD record
ord-4251583a78d44a2db80006d587cd233b
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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