Sodium Chloride → HCID 14674053, compound

HRID 2372425Notes

Reaction equation

HRID 2372425 reaction equation
C[Si](C)(C)[CH:3]1[S:8][CH2:7][CH2:6][CH2:5][S:4]1.CCCCCC.C([Li])CCC.[CH3:22][C:23]([C:25]1[CH:30]=[CH:29][C:28]([O:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[CH:27][CH:26]=1)=O.[Cl-].[Na+]>O1CCCC1>[O:31]([C:28]1[CH:27]=[CH:26][C:25]([C:23](=[C:3]2[S:8][CH2:7][CH2:6][CH2:5][S:4]2)[CH3:22])=[CH:30][CH:29]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 8058HexaneHCID 834132-Trimethylsilyl-1,3-dithianeHCID 2367834'-PhenoxyacetophenoneHCID 178418339Butyllithium

Product 1

HCID 14674053HCID 14674053, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2-Trimethylsilyl-1,3-dithiane, 1.92 g, was dissolved in 20 ml of tetrahydrofuran and 6.3 ml of 1.6 mole hexane solution of n-butyl lithium was dropwise added to the solution in an argon flow under ice cooling. The mixture was stirred at the same temperature for 30 minutes. Then, a solution of 2.33 g of 4-phenoxyacetophenone in 10 ml of tetrahydrofuran was dropwise added under ice cooling followed by stirring at the same temperature for 30 minutes and at room temperature for an hour. After saturated sodium chloride aqueous solution was added, the mixture was extracted with chloroform. After drying the chloroform phase over magnesium sulfate, the solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate : hexane =1 : 10) to give 2.7 g of the oily product.

Workup

  1. stirringby stirring at the same temperature for 30 minutes and at room temperature for an hour
  2. extractionthe mixture was extracted with chloroform
  3. dry with materialAfter drying the chloroform phase over magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate : hexane =1 : 10)

Sources & evidence

ORD record
ord-28213576885f49abb1df0dcba7737298
Source dataset
uspto-grants-1992_03
Patent number
US05098928

Reaction notes

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