Azidotrimethylsilane → HCID 178419355, Verbindung

HRID 385747

Reaktionsgleichung

Reaktionsgleichung von HRID 385747
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[CH:9])=[CH:4][CH:3]=1.C[Si]([N:14]=[N+:15]=[N-:16])(C)C.O=C1O[C@H]([C@H](CO)O)C([O-])=C1O.[Na+]>CC(O)(C)C.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:14]=[N:15][NH:16][CH:9]=2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 3

HCID 78378AzidotrimethylsilaneHCID 136603Benzene, 1-bromo-4-ethynyl-HCID 23667548Sodium Ascorbate

Produkt 1

HCID 178419355HCID 178419355, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel4×HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1-Bromo-4-ethynylbenzene (650 mg, 3.59 mmol) and trimethylsilyl azide (3.57 mL, 26.9 mmol) were combined in t-BuOH (5.0 mL) and water (3.0 mL) CuSO4.5H2O (90 mg, 0.36 mmol) in water (1.0 mL) and sodium ascorbate (285 mg, 1.44 mmol) in water (1.0 mL) were added, and the sealed reaction mixture was stirred at 100° C. for 48 h. The mixture was diluted with water and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (dry load, 0-50% EtOAc/hexanes) afforded the title compound as a colorless solid.

Aufarbeitung

  1. customthe sealed reaction mixture
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. dry with materialFlash chromatography (dry load, 0-50% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-e1d2c4c42db4498d8be0729f57f379c5
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

Verknüpfte Notizen

Wird geladen…