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

HRID 2243134

Reaction equation

[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]

Participants

Conditions

Temperature: -78 °C

Procedure

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 18 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.

Workup

temperatureThe solution was slowly warmed to room temperature
stirringstirred 18 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

Sources & evidence

ORD record: ord-1daf8aca97b0450ba554b98204b4f6d9
Source dataset: uspto-grants-2010_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07674813B2

Linked notes

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