Water → 2,2-Difluoro-2-(2-pyridyl)ethylazide
Reaktionsgleichung
FC(F)(F)S(O[CH2:7][C:8]([F:16])([F:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)(=O)=O.[N-:19]=[N+:20]=[N-:21].[Na+].O>CN(C=O)C>[F:15][C:8]([F:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][N:10]=1)[CH2:7][N:19]=[N+:20]=[N-:21]Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 60 °C
Versuchsvorschrift
To a stirred solution of 5.5 g of 2,2-difluoro-2-(2-pyridyl)ethyl trifluoromethanesulfonate I-1-4 in 70 mL of DMF was added 6.74 g (104 mmol) of sodium azide under Ar. The mixture was heated to 60° C. overnight. A second batch was run in the same manner, and after cooling to rt, both reactions were poured into 600 mL of water, and extracted with 3×500 mL of ether. The combined extracts were washed with brine, dried over Na2SO4 and concentrated at reduced pressure to give an oil that was purified by SiO2 (10×6 cm) using hexane 1:3 EtOAc-hexane and 1:1 EtOAc-hexane. The product-containing fractions were concentrated at reduced pressure to give I-1-5 as a yellow oil: 1H NMR (CDCl3) δ4.05 (t, 2H), 7.4-7.45 (m, 1H), 7.73 (d, 1H), 7.83-7.89 (m, 1H), 8.67 (d, 1H).
Aufarbeitung
- temperatureafter cooling to rt
- extractionextracted with 3×500 mL of ether
- washThe combined extracts were washed with brine
- dry with materialdried over Na2SO4
- concentrationconcentrated at reduced pressure
- customto give an oil that
- customwas purified by SiO2 (10×6 cm)
- concentrationThe product-containing fractions were concentrated at reduced pressure
- customto give I-1-5 as a yellow oil
Quellen und Nachweise
- ORD-Eintrag
- ord-801f46c07e284be2bee02ea1422fc40f
- Quelldatensatz
- uspto-grants-2003_08
- Patentnummer
- US06610701B2
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