Reaktion #2480751

ord-c7a985f3e35e473483812ec28ea426dd

Reaktionsgleichung

CSSC
dimethyl disulphide
[Cl-].[NH4+]
NH4Cl
C[CH2][Mg+].[Br-]
EtMgBr
CCCSc1nc(Br)c(Br)n1COCC[Si](C)(C)C
expected product
CCCSc1nc(Br)c(Br)n1COCC[Si](C)(C)C
2n-propylthio 4,5-dibromo 1-[(2-(trimethylsilyl) ethoxy) methyl]1H-imidazole
→
CCCSc1nc(Br)c(SC)n1COCC[Si](C)(C)C
2n-propylthio 4-bromo 5-methylthio 1-[(2-(trimethylsilyl) ethoxy) methyl]1H-imidazole

Edukte

CSSC
dimethyl disulphide
[Cl-].[NH4+]
NH4Cl
C[CH2][Mg+].[Br-]
EtMgBr
—
solution
CCCSc1nc(Br)c(Br)n1COCC[Si](C)(C)C
expected product
CCCSc1nc(Br)c(Br)n1COCC[Si](C)(C)C
2n-propylthio 4,5-dibromo 1-[(2-(trimethylsilyl) ethoxy) methyl]1H-imidazole

Reagenzien

Keine

Lösungsmittel

CCOC(C)=O
AcOEt
CCOCC
ether
C1CCOC1
THF

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITthe reaction medium is left for 1 hour at ambient temperature
  2. 2
    Sonstigedrying
  3. 3
    Sonstigeevaporating to dryness

Vorschrift

2.4 g of the expected product from Stage B is dissolved in 25 cm3 of anhydrous THF. 3 ml of a 3M solution of EtMgBr in ether is added. After 1 hour at ambient temperature, 1.08 cm3 of dimethyl disulphide is added and the reaction medium is left for 1 hour at ambient temperature followed by hydrolysis with saturated NH4Cl, extraction with AcOEt, drying and evaporating to dryness.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05807878uspto-grants-1998_09