(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene → HCID 67703787, compound

HRID 55284Notes

Reaction equation

HRID 55284 reaction equation
[CH3:1][O:2][C:3](=[O:22])[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[N:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:12]([OH:21])=[CH:11][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[N:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[C:12]([O:21][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)=[CH:11][CH:10]=1)=[O:8]

Participants

3

Reactant 2

HCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexeneHCID 541145215-[3-Hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-5-oxopentanoic acid methyl ester

Product 1

HCID 67703787HCID 67703787, compoundYield 48.5%

Procedure

Under the conditions of example 1 D, 70 mg of 5-[3-hydroxy-2-(2-methoxycarbonylethyl)-6-pyridyl]-5-oxopentanoic acid methyl ester is reacted with 58 mg of (1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene, worked up, and the crude product is chromatographed on silica gel with hexane/0-5% ethyl acetate. 52 mg of 5-{2-(2-methoxycarbonylethyl)-3-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-6-pyridyl}-5-oxopentanoic acid methyl ester is obtained as oil.

Workup

  1. customthe crude product is chromatographed on silica gel with hexane/0-5% ethyl acetate

Sources & evidence

ORD record
ord-3eb252dfac5b47889e946ddcaa102616
Source dataset
uspto-grants-1997_04
Patent number
US05624943

Reaction notes

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