Dimethylformamide → 4-(2-Fluorophenyl)-1-methyl-1H-1,2,3-triazole-5-carbaldehyde
Reaktionsgleichung
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:13])[CH:12]=1.[Li]CCCC.CN([CH:22]=[O:23])C.[Cl-].[NH4+]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:9]=[N:10][N:11]([CH3:13])[C:12]=1[CH:22]=[O:23]Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -75 °C
Versuchsvorschrift
To a solution of 4-(2-fluorophenyl)-1-methyl-1H-1,2,3-triazole (1.44 g, 8.1 mmol) in THF (41 mL) was added n-BuLi (1.6 M in hexane, 6.10 mL, 9.8 mmol) dropwise at −75° C. under Argon. The resulted orange solution was stirred at −75° C. for 1 h, then DMF (0.82 mL, 10.6 mmol) was added dropwise at −75° C. and the reaction mixture was allowed to warm up to room temperature over 1 h. The mixture was then poured into saturated ammonium chloride solution and extracted with ethyl acetate and the combined organic extracts washed with brine, dried over sodium sulphate, filtered and evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (1.45 g, 87%) as an off white solid. MS: m/e=206.0 [M]+.
Aufarbeitung
- temperatureto warm up to room temperature over 1 h
- extractionextracted with ethyl acetate
- washthe combined organic extracts washed with brine
- dry with materialdried over sodium sulphate
- filtrationfiltered
- customevaporated
- customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)
Quellen und Nachweise
- ORD-Eintrag
- ord-3755f18473d943d6acb6c400b490b90d
- Quelldatensatz
- uspto-grants-2014_06
- Patentnummer
- US08742097B2
Notizen zur Reaktion
Wird geladen…