Iodoethane → HCID 15037560, compound

HRID 1090435Notes

Reaction equation

HRID 1090435 reaction equation
[Mg].C(I)C.C[Si](C)(C)[O:7][C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][C:9]=1[C:15]1([CH3:20])[O:19]CCO1.[CH3:23][Si:24](Cl)([CH3:26])[CH3:25].CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>O1CCCC1.CCCCCC.CCOC(C)=O.CC(C)=O.O>[OH:7][C:8]1[CH:13]=[CH:12][C:11]([Si:24]([CH3:26])([CH3:25])[CH3:23])=[CH:10][C:9]=1[C:15](=[O:19])[CH3:20]

Participants

10

Reactant 5

HCID 6340IodoethaneHCID 6397ChlorotrimethylsilaneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 5462224MagnesiumHCID 15037558HCID 15037558, compound

Product 1

HCID 15037560HCID 15037560, compoundYield 67%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×HCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 321 mg (13.2 mmol) of magnesium, 0.07 ml of ethyl iodide and 1.32 ml of dry tetrahydrofuran was refluxed. After cooling, the mixture was diluted with 3.96 ml of dry tetrahydrofuran and refluxed. To the mixture was added dropwise a solution 4.0 g of crude 2-(2-trimethylsilyloxy-5-bromophenyl)-2-methyl-1,3-dioxolane, obtained as above, in 9.6 ml of tetrahydrofuran and the reaction mixture was refluxed for 2 hours. After cooling, 1.68 ml (13.2 mmol) of trimethylsilyl chloride was added and refluxed for 3 hours. Water was added to the reaction mixture. The mixture was extracted with ether. The extract was washed with water and sat.aq.NaCl, dried over anhyd.Na2SO4 and evaporated. To the residue was added 72 ml of acetone, 10.8 ml (600 mmol) of water and 0.46 g (1.8 mmol) of PPTS. The mixture was refluxed for 3 hours and evaporated. The residue was dissolved in ether. The solution was washed with water, aqueous sodium bicarbonate solution and sat.aq.NaCl, dried over anhyd.Na2SO4 and evaporated. The residue was purified by column chromatography on silica gel [eluent: n-hexane-AcOEt (20:1)] to 1.66 g of pale yellow liquid (yield 67%).

Workup

  1. temperaturewas refluxed
  2. temperatureAfter cooling
  3. temperaturerefluxed
  4. temperaturethe reaction mixture was refluxed for 2 hours
  5. temperatureAfter cooling
  6. temperaturerefluxed for 3 hours
  7. extractionThe mixture was extracted with ether
  8. washThe extract was washed with water and sat.aq
  9. dry with materialNaCl, dried over anhyd
  10. customNa2SO4 and evaporated
  11. temperatureThe mixture was refluxed for 3 hours
  12. customevaporated
  13. dissolutionThe residue was dissolved in ether
  14. washThe solution was washed with water, aqueous sodium bicarbonate solution and sat.aq
  15. dry with materialNaCl, dried over anhyd
  16. customNa2SO4 and evaporated

Sources & evidence

ORD record
ord-5ce100677a4e4b638e89933e4e41eb60
Source dataset
uspto-grants-1992_01
Patent number
US05081271

Reaction notes

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