Sodium Iodide → 2-Benzo[1,3]dioxol-5-ylmethyl-3-oxo-3-phenylpropionate ethyl ester

HRID 17880

Reaction equation

HRID 17880 reaction equation
Cl[CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[C:20]([CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[CH2:32]([O:31][C:29](=[O:30])[CH:28]([CH2:2][C:3]1[CH:11]=[CH:10][C:6]2[O:7][CH2:8][O:9][C:5]=2[CH:4]=1)[C:20](=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[CH3:33]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7170Ethyl benzoylacetateHCID 11430Potassium CarbonateHCID 887131,3-Benzodioxole, 5-(chloromethyl)-

Product 1

HCID 686974762-Benzo[1,3]dioxol-5-ylmethyl-3-oxo-3-phenylpropionate ethyl esterYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Chloromethyl benzo[1,3]dioxol (11.2 g, 65.7 mmol) was dissolved in Dimethylformamide. Then, potassium carbonate (18.2 g, 131.4 mmol), sodium iodide (10.8 g, 72.27 mmol) and ethyl benzoylacetate (12.5 ml, 72.27 mmol) were added thereto and stirred for 5 hours at room temperature. The reaction mixture was extracted with ammonium chloride and ether, the organic layer was separated, dried over anhydrous magnesium sulfate, concentrated, and the resulting residue was purified by column chromatography to obtain 2-benzo[1,3]dioxol-5-ylmethyl-3-oxo-3-phenylpropionate ethyl ester (16.4 g, 76%).

Workup

  1. extractionThe reaction mixture was extracted with ammonium chloride and ether
  2. customthe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customthe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-0ca0b1d62b744f8496166b2efb4398a0
Source dataset
uspto-grants-2010_06
Patent number
US07741323B2

Linked notes

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