1,8-Diazabicyclo(5.4.0)undec-7-ene → 3-Azidomethyl-5-trifluoromethyl-benzonitrile
Reaktionsgleichung
O[CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7].C1(P([N:29]=[N+:30]=[N-:31])(C2C=CC=CC=2)=O)C=CC=CC=1.C1CCN2C(=NCCC2)CC1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[N:29]([CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:10]=1)[C:6]#[N:7])=[N+:30]=[N-:31]Komponenten
6
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A solution of 3-hydroxymethyl-5-trifluoromethyl-benzonitrile (200 mg, 0.994 mmol) in toluene (1 ml) at 0° C. was treated with diphenyl phosphoryl azide (328 mg, 1.19 mmol), followed by DBU (182 mg, 1.19 mmol) and stirred at 0° C. for 2 hours. The ice bath was removed and the reaction was stirred at room temperature for overnight. Reaction was diluted with ethyl acetate and washed with 10% HCl solution, dried over anhydrous magnesium sulphate and concentrated in vacuo. The residue was purified by silica gel chromatography over 12+S Biotage silica column (eluted with 0-30% ethyl acetate in hexanes) to yield the title compound (150 mg, 67%) as a colorless oil. 1H NMR (400 MHz, CDCl3) δ ppm 4.54 (s, 2H) 7.82 (s, 2H) 7.88 (s, 1H).
Aufarbeitung
- customThe ice bath was removed
- stirringthe reaction was stirred at room temperature for overnight
- customReaction
- washwashed with 10% HCl solution
- dry with materialdried over anhydrous magnesium sulphate
- concentrationconcentrated in vacuo
- customThe residue was purified by silica gel chromatography over 12+S Biotage silica column (eluted with 0-30% ethyl acetate in hexanes)
Quellen und Nachweise
- ORD-Eintrag
- ord-bcf0179af5734096af11c4b840bce971
- Quelldatensatz
- uspto-grants-2011_04
- Patentnummer
- US07919506B2
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