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Water → HCID 59643020, compound

HRID 2251615
Notes
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Reaction equation

HRID 2251615 reaction equation
I[C:2]1[CH:3]=[C:4]([O:14][CH3:15])[C:5]([O:12][CH3:13])=[C:6]([CH:11]=1)[C:7]([O:9][CH3:10])=[O:8].O.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([S:23]([O-:25])=[O:24])=[CH:19][CH:18]=1.[Na+].O.CCOC(C)=O>CN(C=O)C.[Cu]I>[CH3:13][O:12][C:5]1[C:4]([O:14][CH3:15])=[CH:3][C:2]([S:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=2)(=[O:25])=[O:24])=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10314022HCID 10314022, compoundHCID 23682957Sodium 4-methylbenzene-1-sulfinate hydrate

Product 1

HCID 59643020HCID 59643020, compound

Reagents, catalysts & solvents 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
Catalyst
HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of methyl 5-iodo-2,3-dimethoxy-benzoate (2.25 g, 7.0 mmol) in 20 mL DMF, sodium p-toluenesulfinate hydrate (2.21 g, 11.26 mmol, 1.6 eq.) and CuI (2.22 g, 11.6 mmol, 1.66 eq.) were added and light green solution was stirred at 110° C. for 14 h. H2O and EtOAc were then added to the mixture and the phases were separated. The organic layer was washed with saturated NaCl solution, dried over MgSO4 and evaporated under reduced pressure. The crude product was purified using flash chromatography (silica gel, hexane/EtOAc 8:2→3:2) to yield the desired product as a colorless solid.

Workup

  1. customthe phases were separated
  2. washThe organic layer was washed with saturated NaCl solution
  3. dry with materialdried over MgSO4
  4. customevaporated under reduced pressure
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-8ab6a9ef90f245f8b27c6b8b2686bb4e
Source dataset
uspto-grants-2008_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07319101B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes