1,2-Dimethoxyethane → HCID 23365812, Verbindung

HRID 129513

Reaktionsgleichung

Reaktionsgleichung von HRID 129513
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]

Komponenten

8

Edukt 4

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

Produkt 1

HCID 23365812HCID 23365812, VerbindungAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 8058HexaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-4886fc6c00284f27b3cec637fc1a9d33
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05468768

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