Sodium Iodide → HCID 54189192, compound

HRID 1779798Notes

Reaction equation

HRID 1779798 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]2[O:14][CH2:13][CH:12](O)[O:11][C:10]=2[CH:16]=1)=[O:5])[CH3:2].[C:17](=[O:20])([O-])[O-].[Cs+].[Cs+].C(Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[I-].[Na+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[C:8]([O:20][CH2:17][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:9]2[O:14][CH2:13][CH2:12][O:11][C:10]=2[CH:16]=1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 54349018HCID 54349018, compound

Product 1

HCID 54189192HCID 54189192, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The reaction mixture containing 900 ml of acetone, 17.4 g of hydroxy-1,4-benzodioxane-7-carboxylic acid ethyl ester, 37.9 g of caesium carbonate, 11 ml of benzyl bromide and 7.7 g of sodium iodide is stirred under reflux for 3 hours and then concentrated by evaporation. The residue is partitioned between diethyl ether and water. The organic phases are dried over sodium sulfate and concentrated by evaporation. The title compound is obtained from the residue by FC (900 g of silica gel, hexane/ethyl acetate=1:1): Rf (hexane/ethyl acetate=2:1)=0.36.

Workup

  1. temperatureunder reflux for 3 hours
  2. concentrationconcentrated by evaporation
  3. customThe residue is partitioned between diethyl ether and water
  4. dry with materialThe organic phases are dried over sodium sulfate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-0bced3b33b8d49e1963efdccc042540d
Source dataset
uspto-grants-1997_05
Patent number
US05627182

Reaction notes

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