Water → Ethyl(6-((2,4-dichlorobenzyl)sulfinyl)-1-benzothiophen-3-yl)acetate

HRID 591488Notes

Reaction equation

HRID 591488 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([S:15][CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2].O.[O-:27]S([O-])(=S)=O.[Na+].[Na+]>CC#N>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[C:10]2[CH:11]=[CH:12][C:13]([S:15]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][C:18]=3[Cl:24])=[O:27])=[CH:14][C:9]=2[S:8][CH:7]=1)[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 24477Sodium ThiosulfateHCID 118667019Ethyl(6-((2,4-dichlorobenzyl)sulfanyl)-1-benzothiophen-3-yl)acetate

Product 1

HCID 118667020Ethyl(6-((2,4-dichlorobenzyl)sulfinyl)-1-benzothiophen-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of ethyl(6-((2,4-dichlorobenzyl)sulfanyl)-1-benzothiophen-3-yl)acetate (315 mg), water (3.00 mL) and CH3CN (3.00 mL) was added NaIO4 (164 mg) at room temperature. The mixture was stirred at room temperature for 1 day. To the mixture was added NaIO4 (164 mg), and the mixture was stirred for further 1 day. To the mixture was added saturated aqueous Na2S2O3 at room temperature, and the mixture was extracted with EtOAc. The organic layer was washed with brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (204 mg). The residue was recrystallized from EtOAc-hexane to give the title compound.

Workup

  1. stirringthe mixture was stirred for further 1 day
  2. extractionthe mixture was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-998e3555062b434c886255604138adbe
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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