Sodium Iodide → HCID 54189192, compound

HRID 2256708Notes

Reaction equation

HRID 2256708 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-e342eba3fc904642bb0fb37933ab736f
Source dataset
uspto-grants-1997_08
Patent number
US05654445

Reaction notes

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