Sodium Iodide → 2-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl tert-butyldimethylsilyl ether

HRID 1588134Notes

Reaction equation

HRID 1588134 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]([O:13][CH3:14])=[CH:5][C:4]=1[O:15][CH2:16][O:17][CH3:18].C([Li])(CC)C.[Si:24]([O:31][CH2:32][CH2:33]Br)([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25].[I-].[Na+]>O1CCCC1.C(OCC)C.C1C=CC=CC=1.CN(C)P(=O)(N(C)C)N(C)C>[Si:24]([O:31][CH2:32][CH2:33][C:5]1[C:4]([O:15][CH2:16][O:17][CH3:18])=[C:3]([O:2][CH3:1])[CH:8]=[C:7]([O:9][CH2:10][O:11][CH3:12])[C:6]=1[O:13][CH3:14])([C:27]([CH3:30])([CH3:29])[CH3:28])([CH3:26])[CH3:25]

Participants

9

Reactant 4

HCID 5238Sodium IodideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 10061046HCID 10061046, compoundHCID 178418400CID 53628100

Product 1

HCID 197572472-[2,5-Dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl tert-butyldimethylsilyl ether

Reagents, catalysts & solvents 4

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Conditions

Temperature
-78 °C

Procedure

126 Milligrams of 1,4-dimethoxy-2,5-bis(methoxymethoxy)benzene was dissolved in 2 ml of anhydrous tetrahydrofuran, then 0.2 ml of hexamethylphosphoric triamide was added to the solution and whole mixture was cooled to -78° C. in a dry ice-acetone bath. Under argon gas stream conditions, 0.5 ml of sec-butyllithium was added dropwise to the reaction mixture and stirred for 30 minutes. Then 140 mg of 2-bromoethyl tert-butyldimethylsilyl ether and 70 mg of anhydrous sodium iodide were added to the reaction mixture and was stirred at -78° C. for 4 hours, then the temperature was elevated to room temperature. The solvent was removed by evaporation under reduced pressure, then to the residue thus obtained were added 50 ml of benzene and 50 ml of diethyl ether, the organic layer was washed three times with 30 ml of water, then washed three times with 30 ml of a saturated sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. The solvent was removed by evaporation under reduced pressure, then the residue was treated on a silica gel thin layer chromatography, and purified by developing with 30% ethyl acetate-n-hexane mixed solvent to yield 15.0 mg of 2-[2,5-dimethoxy-3,6-bis(methoxymethoxy)phenyl]ethyl tert-butyldimethylsilyl ether. Colorless oily substance.

Workup

  1. stirringwas stirred at -78° C. for 4 hours
  2. customwas elevated to room temperature
  3. customThe solvent was removed by evaporation under reduced pressure
  4. customto the residue thus obtained
  5. washthe organic layer was washed three times with 30 ml of water
  6. washwashed three times with 30 ml of a saturated sodium chloride aqueous solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was removed by evaporation under reduced pressure
  9. additionthe residue was treated on a silica gel thin layer chromatography
  10. custompurified

Sources & evidence

ORD record
ord-032285c900b9415a902a3d1da459ce45
Source dataset
uspto-grants-1993_06
Patent number
US05220042

Reaction notes

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