Ethyl acetate hexane → HCID 131730128, compound

HRID 400330Notes

Reaction equation

HRID 400330 reaction equation
[N+:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]=1[S:13]([O-:16])(=[O:15])=[O:14])([O-:3])=[O:2].C(=O)([O-])[O-].[Ag+2:21].CCCCCC.C(OCC)(=O)C>C(#N)C.O>[N+:1]([C:4]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]=1[S:13]([O-:16])(=[O:14])=[O:15])([O-:3])=[O:2].[Ag+:21]

Participants

6

Reactant 3

HCID 21226206Ethyl acetate hexaneHCID 58363877HCID 58363877, compoundHCID 178418647HCID 178418647, compound

Product 1

HCID 131730128HCID 131730128, compoundYield 98.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of mono nitro-benzothiophene-2-sulfonate (0.5177 g, 1.86 mmol) in 50 mL of acetonitrile and 1 mL of water was added silver carbonate (0.6169 g, 2.24 mmol) in portions in darkness. The resulting suspension was stirred overnight for 9 days, until no starting material is shown on the thin layer chromatography with an eluent of hexane/ethyl acetate (1:4). The mixture was filtered through half an inch of Celite® and the solid was washed with 3×40 mL acetonitrile. The organic filtrate was combined and organic solvent was removed via rotary evaporator to dryness and thus afforded 0.668 g of viscous solid with a yield of 98.2%. The resulting compound was not purified for further reactions.

Workup

  1. filtrationThe mixture was filtered through half an inch of Celite®
  2. washthe solid was washed with 3×40 mL acetonitrile
  3. customorganic solvent was removed via rotary evaporator to dryness and thus afforded 0.668 g of viscous solid with a yield of 98.2%
  4. customThe resulting compound was not purified for further reactions

Sources & evidence

ORD record
ord-36e5bf45260245b080ad551cf31c75a1
Source dataset
uspto-grants-2014_06
Patent number
US08741545B2

Reaction notes

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