Azidotrimethylsilane → HCID 178487641, Verbindung

HRID 915905Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915905
[CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]\[N+:11]([O-])=O)[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.[Si]([N:24]=[N+:25]=[N-])(C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:24]=[N:25][NH:11][CH:10]=2)[CH:6]=[CH:5][C:4]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1

Komponenten

5

Edukt 3

HCID 78378AzidotrimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 68881182HCID 68881182, Verbindung

Produkt 1

HCID 178487641HCID 178487641, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 2-{2-methoxy4-[(Z)-2-nitroethenyl]phenyl}pyridine (0.23 g, 0.89 mmol) and TMSN3 (0.18 mL, 1.34 mmol) in DMF (1 mL) was heated to slowly to 50° C. while TBAF (0.98 mL, 1.0 M in THF, 0.98 mol) was added dropwise over 20 min. The resulting reaction mixture was continued to stir at 50° C. for 30 min. The mixture was partitioned between sat. NaHCO3 (20 mL) and EtOAc (60 mL). The phases were separated and the aqueous layer was extracted with EtOAc (3×60 mL). The combined organic layers were dried (MgSO4), filtered and concentrated. The residue was purified on silica gel (20:1 hexane-ethyl acetate) to afford a yellow solid.

Aufarbeitung

  1. additionwas added dropwise over 20 min
  2. customThe resulting reaction mixture
  3. customThe mixture was partitioned between sat. NaHCO3 (20 mL) and EtOAc (60 mL)
  4. customThe phases were separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×60 mL)
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel (20:1 hexane-ethyl acetate)
  10. customto afford a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-d71f459474f448798b53a85f4873100b
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268151B2

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