Sodium Azide → (4-Azidobut-1-ynyl)triethylsilane

HRID 58640Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58640
[N-:1]=[N+:2]=[N-:3].[Na+].CC1C=CC(S(O[CH2:16][CH2:17][C:18]#[C:19][Si:20]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH2:21][CH3:22])(=O)=O)=CC=1>CN(C=O)C>[N:1]([CH2:16][CH2:17][C:18]#[C:19][Si:20]([CH2:25][CH3:26])([CH2:21][CH3:22])[CH2:23][CH3:24])=[N+:2]=[N-:3]

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 120301384-(Triethylsilyl)but-3-yn-1-yl 4-methylbenzene-1-sulfonate

Produkt 1

HCID 86663839(4-Azidobut-1-ynyl)triethylsilaneAusbeute 103,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Sodium azide (1.80 g; 27.65 mmol) was added to a solution of 4-(triethylsilyl)but-3-ynyl 4-methylbenzenesulfonate (3.12 g; 9.22 mmol) in DMF (15 mL) and stirred at 60° C. for 3 hours. After cooling, the volatiles were removed under reduced pressure and the residue was partitioned between saturated ammonium chloride and ethyl acetate. The organic layer was dried and concentrated under reduced pressure to afford 2.0 g (quantitative yield) of (4-azidobut-1-ynyl)triethylsilane as a colorless oil.

Aufarbeitung

  1. temperatureAfter cooling
  2. customthe volatiles were removed under reduced pressure
  3. customthe residue was partitioned between saturated ammonium chloride and ethyl acetate
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-83eb10e8740f4a2c89ba0f4d6f2e6b50
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434722B2

Notizen zur Reaktion

Wird geladen…