Cesium carbonate → Ethyl 2-(2,6-dichloro-4-hydroxymethylphenoxy)-2-(3,4-methylene dioxyphenyl)acetate

HRID 1741755Notes

Reaction equation

HRID 1741755 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:11])[C:9]=1[OH:10])[CH2:5][OH:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH:19]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([Cl:11])[C:9]=1[O:10][CH:19]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)[C:20]([O:22][CH2:23][CH3:24])=[O:21]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 176409Benzenemethanol, 3,5-dichloro-4-hydroxy-HCID 15383768Ethyl alpha-bromo-3,4-methylenedioxyphenylacetate

Product 1

HCID 53743625Ethyl 2-(2,6-dichloro-4-hydroxymethylphenoxy)-2-(3,4-methylene dioxyphenyl)acetateYield 86.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 0.120 g (0.62 mmol) of 3,5-dichloro-4-hydroxybenzyl alcohol in 1.5 mL DMF was added 0.223 g (0.68 mmol) of cesium carbonate and the reaction was magnetically stirred at room temperature for 15 minutes. A solution of 0.196 g (0.68 mmol) of ethyl α-bromo-3,4-methylenedioxyphenylacetate in 0.5 mL DMF was added and the reaction was stirred an additional 30 minutes at room temperature. The reaction mixture was partitioned between EtOAc and 5% aqueous citric acid, extracted, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 30% EtOAc-hexane, and evaporation of the purified fractions afforded 0.214 g (86%) of the title compound.

Workup

  1. stirringthe reaction was stirred an additional 30 minutes at room temperature
  2. customThe reaction mixture was partitioned between EtOAc and 5% aqueous citric acid
  3. extractionextracted
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified on a silica gel flash chromatography column
  8. washeluted with 30% EtOAc-hexane, and evaporation of the purified fractions

Sources & evidence

ORD record
ord-300c1a4574fc4c6787c801eeca321d3c
Source dataset
uspto-grants-1994_08
Patent number
US05334598

Reaction notes

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