Dimethylformamide → HCID 11131912, Verbindung

HRID 433593Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 433593
[I:1][C:2]1[N:3]=[CH:4][N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=1I.C([Li])CCC.CN([CH:24]=[O:25])C.[NH4+].[Cl-]>C1COCC1>[I:1][C:2]1[N:3]=[C:4]([CH:24]=[O:25])[N:5]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:6]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 11091612HCID 11091612, VerbindungHCID 178418339Butyllithium

Produkt 1

HCID 11131912HCID 11131912, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

A solution of 4,5-diiodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-imidazole (8.86 g, 19.68 mmol) in anhydrous THF (110 ml) under argon was cooled to −78° C. and was treated dropwise with n-butyllithium (13.5 ml, 21.65 mmol, 1.6M in hexane). After 10 minutes stirring at −78°° C. and 30 minutes at 45° C., the reaction mixture was cooled to −78° C. and treated at once with DMF (10 ml). The mixture was allowed to warm to room temperature and saturated NH4Cl (150 ml) was added. The aqueous layer was extracted 2 times with AcOEt. The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo. The residue was chromatographed (silica, elution with hexane/AcOEt=98:2) to provide the title compound (5.18 g, 75%) as a light yellow oil. MS: m/e=352.1 (M+).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. extractionThe aqueous layer was extracted 2 times with AcOEt
  3. dry with materialThe combined extracts were dried over Na2SO4
  4. filtrationfiltered
  5. customthe solvent was removed in vacuo
  6. customThe residue was chromatographed
  7. wash(silica, elution with hexane/AcOEt=98:2)

Quellen und Nachweise

ORD-Eintrag
ord-f7da3c9bbb9246a3ba0f44323cf2efbc
Quelldatensatz
uspto-grants-2003_12
Patentnummer
US06667335B2

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