Sodium Iodide → HCID 20636318, compound

HRID 49329

Reaction equation

HRID 49329 reaction equation
CS([O:5][CH2:6][C:7]1[S:8][C:9]([C:12]2([CH2:17][CH3:18])[O:16][CH2:15][CH2:14][O:13]2)=[CH:10][CH:11]=1)(=O)=O.O[C:20]1[CH:21]=[C:22]([C:30]([O:32][CH3:33])=[O:31])[C:23](=[CH:28][CH:29]=1)[C:24]([O:26][CH3:27])=[O:25].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CC(=O)CC>[CH2:17]([C:12]1([C:9]2[S:8][C:7]([CH2:6][O:5][C:29]3[CH:28]=[C:23]([C:24]([O:26][CH3:27])=[O:25])[C:22](=[CH:21][CH:20]=3)[C:30]([O:32][CH3:33])=[O:31])=[CH:11][CH:10]=2)[O:16][CH2:15][CH2:14][O:13]1)[CH3:18]

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 89726Dimethyl 4-hydroxyphthalateHCID 206363015-(2-Ethyl-[1,3]dioxolan-2-yl)-2-thienylmethyl methanesulphonate

Product 1

HCID 20636318HCID 20636318, compound

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

9.25 g (43.2 mmol) of 5-(2-ethyl-[1,3]dioxolan-2-yl)-2-thienylmethyl methanesulphonate are dissolved in 100 mL of 2-butanone, and 9.07 g (43.2 mmol) of dimethyl 4-hydroxyphthalate (prepared in Example 1(b)), 6 g of potassium carbonate (43.2 mmol) and 20 mg of sodium iodide are added. The mixture is refluxed for 12 hours, cooled and filtered. The filtrate is concentrated under reduced pressure and then purified by chromatography on a column of silica. A yellow oil is obtained (m=12.70 g; Y=73%).

Workup

  1. temperatureThe mixture is refluxed for 12 hours
  2. temperaturecooled
  3. filtrationfiltered
  4. concentrationThe filtrate is concentrated under reduced pressure
  5. custompurified by chromatography on a column of silica
  6. customA yellow oil is obtained (m=12.70 g; Y=73%)

Sources & evidence

ORD record
ord-3398eeb0de564ba9ab1b8cc49873e73a
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Linked notes

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