(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene → HCID 19957426, compound

HRID 55294Notes

Reaction equation

HRID 55294 reaction equation
[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][C:9]1[C:14]([OH:15])=[CH:13][CH:12]=[C:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[N:10]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]/[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH3:38])=[CH:33][CH:32]=1>>[C:1]([O:5][C:6](=[O:23])[CH2:7][CH2:8][C:9]1[C:14]([O:15][CH2:25][CH2:26][CH2:27][CH2:28]/[CH:29]=[CH:30]/[C:31]2[CH:32]=[CH:33][C:34]([O:37][CH3:38])=[CH:35][CH:36]=2)=[CH:13][CH:12]=[C:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[N:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexeneHCID 19957432HCID 19957432, compound

Product 1

HCID 19957426HCID 19957426, compoundYield 50.3%

Procedure

Under the conditions of example 1 D, 440 mg of 3-(6-tert-butoxycarbonyl-3-hydroxy-2-pyridyl)-propionic acid-tert-butyl ester is reacted with 367 mg of (1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene, worked up, and the crude product is chromatographed on silica gel with hexane/0-8% ethyl acetate. 350 mg of 3-{6-tert-butoxycarbonyl-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-2-pyridyl}-propionic acid-tert-butyl ester is obtained as oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-8% ethyl acetate

Sources & evidence

ORD record
ord-577d5dfb64c542c4bf4eb8a00cefcd42
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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