(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene → HCID 67794837, compound

HRID 1707293Notes

Reaction equation

HRID 1707293 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:10]=1)=[O:8].Br[CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1>>[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:24][CH2:25][CH2:26][CH2:27]/[CH:28]=[CH:29]/[C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)=[C:11]([CH2:16][CH2:17][C:18]([O:20][CH3:21])=[O:19])[CH:10]=1)=[O:8]

Participants

3

Reactant 2

HCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexeneHCID 54148678HCID 54148678, compound

Product 1

HCID 67794837HCID 67794837, compoundYield 81.7%

Procedure

Under the conditions of example 1A, 500 mg of 5-[4-hydroxy-3-(2-methoxycarbonylethyl)-Phenyl]-5-oxo-pentanoic acid methyl ester is reacted with 436 mg of (1E)-6-bromo-l-(4-methoxyphenyl)-1-hexene, worked up and the crude product is chromatographed on silica gel with hexane/ethyl acetate (0-15% ethyl acetate). 657 mg of 5-[3-(2-methoxycarbonylethyl)-4-[6-(4-methoxyphenyl)-( 5E)-5-hexenyloxy]-phenyl]-5-oxo-pentanoic acid methyl ester is obtained as oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/ethyl acetate (0-15% ethyl acetate)

Sources & evidence

ORD record
ord-03de6b521f834a67851d6cb0e255b447
Source dataset
uspto-grants-1994_10
Patent number
US05352701

Reaction notes

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