Lithium Carbonate → 5-(3-hydroxy-4-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-phenyl}-5-oxopentanoic acid methyl ester

HRID 1707299Notes

Reaction equation

HRID 1707299 reaction equation
[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([OH:16])[CH:10]=1)=[O:8].C(=O)([O-])[O-].[Li+].[Li+].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>CN(C)C=O>[CH3:1][O:2][C:3](=[O:17])[CH2:4][CH2:5][CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([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)=[C:11]([OH:16])[CH:10]=1)=[O:8]

Participants

5

Reactant 3

HCID 11125Lithium CarbonateHCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexeneHCID 231781405-(3,4-Dihydroxyphenyl)-5-oxo-pentanoic acid methyl ester

Product 1

HCID 231781395-(3-hydroxy-4-[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-phenyl}-5-oxopentanoic acid methyl esterYield 14.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under the conditions of example 2C, 1.8g of 5-(3,4-dihydroxyphenyl)-5-oxo-pentanoic acid methyl ester in 19 ml of dimethylformamide is reacted in the presence of 1.4g of lithium carbonate with 2.05g of (1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene, worked up and chromatographed. 470 mg of 5-(3-hydroxy-4[6-(4-methoxyphenyl)-(5E)-5-hexenyloxy]-phenyl)-5-oxo-pentanoic acid methyl ester of melting point 78°-80° C. is obtained.

Workup

  1. customchromatographed

Sources & evidence

ORD record
ord-c2db099cd9fa4c08bf82a6964e21323f
Source dataset
uspto-grants-1994_10
Patent number
US05352701

Reaction notes

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