2-Ethylbutyraldehyde → 2-Ethyl-1-[1-(4-fluorobenzyl)-1H-1,2,4-triazol-5-yl]butan-1-ol

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Reaktionsgleichung

[F:1][C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]2[CH:11]=[N:10][CH:9]=[N:8]2)=[CH:4][CH:3]=1.C([Li])CCC.[CH2:19]([CH:21]([CH2:24][CH3:25])[CH:22]=[O:23])[CH3:20]>C1COCC1>[CH2:19]([CH:21]([CH2:24][CH3:25])[CH:22]([C:11]1[N:7]([CH2:6][C:5]2[CH:12]=[CH:13][C:2]([F:1])=[CH:3][CH:4]=2)[N:8]=[CH:9][N:10]=1)[OH:23])[CH3:20]

Komponenten

Reaktionsbedingungen

Temperatur: -78 °C

Versuchsvorschrift

To a stirred solution of 1-(4-fluorobenzyl)-1H-1,2,4-triazole (0.500 g, 2.82 mmol) in THF (30 mL) at −78° C. was added a solution of n-butyllithium (2.5M in hexanes, 1.1 mL, 2.9 mmol) dropwise. The mixture was stirred at −78° C. for 1.5 h, then 2-ethylbutyraldehyde (0.42 mL, 3.4 mmol) was added. The solution was slowly warmed to room temperature and stirred i 8 h. It was then quenched with saturated aqueous NH4Cl and extracted twice with EtOAc. The organic extracts were dried (MgSO4), filtered, concentrated in vacuo and purified by column chromatography (SiO2, EtOAc/hexane, 1:1) to yield an oil in 47% yield.

Aufarbeitung

temperatureThe solution was slowly warmed to room temperature
stirringstirred i 8 h
customIt was then quenched with saturated aqueous NH4Cl
extractionextracted twice with EtOAc
dry with materialThe organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
custompurified by column chromatography (SiO2, EtOAc/hexane, 1:1)
customto yield an oil in 47% yield

Quellen und Nachweise

ORD-Eintrag: ord-90dc9990adc849ed83b9651920a2e860
Quelldatensatz: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07399778B2

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