1,2-Dimethoxyethane → HCID 23365812, compound

HRID 129513

Reaction equation

HRID 129513 reaction equation
COCCOC.I[C:8]1[CH:13]=[C:12]([CH2:14][S:15]([CH3:18])(=[O:17])=[O:16])[CH:11]=[CH:10][C:9]=1[NH2:19].[CH3:20][Si:21]([C:24]#[C:25][Si](C)(C)C)([CH3:23])[CH3:22].C([O-])([O-])=O.[Na+].[Na+]>CCCCCC.CCOC(C)=O.CO>[CH3:18][S:15]([CH2:14][C:12]1[CH:13]=[C:8]2[C:9](=[CH:10][CH:11]=1)[NH:19][C:24]([Si:21]([CH3:23])([CH3:22])[CH3:20])=[CH:25]2)(=[O:17])=[O:16]

Participants

8

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 84564Bis(trimethylsilyl)acetyleneHCID 193717842-Iodo-4-[(methylsulfonyl)methyl]benzenamine

Product 1

HCID 23365812HCID 23365812, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1,2-dimethoxyethane (DME, 70 mL) was added 2 -iodo-4-[(methylsulfonyl)methyl]benzenamine (1) (1.9 g, 0.0061 mol), bis(trimethylsilyl) acetylene (1.56 g, 0.00915 mol), tetrakistriphenylphosphine Pd(O) (0.705 g, 0.00061 mol) and saturated aqueous Na2CO3 (5 mL). The reaction was heated at reflux for 48 h. The solvent was removed in vacuo and the residue was dissolved in EtOAc and washed with brine. The organic layer was dried over MgSO4, filtered and evaporated to give the crude product. Silica gel chromatography (20-100% EtOAc gradient in hexane followed by 5-10% MeOH gradient in EtOAc) of the concentrate afforded the product (2) (1.42 g, 83%) as a brown oil.

Workup

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 48 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in EtOAc
  5. washwashed with brine
  6. dry with materialThe organic layer was dried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto give the crude product

Sources & evidence

ORD record
ord-4886fc6c00284f27b3cec637fc1a9d33
Source dataset
uspto-grants-1995_11
Patent number
US05468768

Linked notes

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