Cesium carbonate → HCID 67797294, compound

HRID 1707287Notes

Reaction equation

HRID 1707287 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:7][O:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18].Br[CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]/[C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][CH:28]=1>CN(C)C=O>[CH3:7][O:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18][CH2:21][CH2:22][CH2:23][CH2:24]/[CH:25]=[CH:26]/[C:27]1[CH:28]=[CH:29][C:30]([O:33][CH3:34])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 2794569Methyl 3-(2-hydroxyphenyl)propionateHCID 15472944(1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene

Product 1

HCID 67797294HCID 67797294, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

651 mg of cesium carbonate is added to a solution of 180 mg of 3-(2-hydroxyphenyl)-propionic acid methyl ester and 272 mg of (1E)-6-bromo-1-(4-methoxyphenyl)-1-hexene in 2 ml of dimethylformamide and the suspension is stirred for 16 hours at room temperature. The reaction mixture is filtered, the filtration residue is washed with dichloromethane, the filtrate concentrated by evaporation and the residue chromatographed on silica gel with hexane. 255 mg of 3-[2-[6-(4-methoxyphenyl)(5E)-5-hexenyloxy]-phenyl]-propionic acid methyl ester is obtained as oil.

Workup

  1. filtrationThe reaction mixture is filtered
  2. washthe filtration residue is washed with dichloromethane
  3. concentrationthe filtrate concentrated by evaporation
  4. customthe residue chromatographed on silica gel with hexane

Sources & evidence

ORD record
ord-f7032184703a4c99a3f25efa6b528651
Source dataset
uspto-grants-1994_10
Patent number
US05352701

Reaction notes

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