1H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]- → 2-n-butyl-1-(2-chlorophenyl)methyl-5-(a-hydroxy) ethyl-1H-imidazole

HRID 260738

Reaction equation

[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]([CH:10]=[O:11])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[CH3:20][Li]>O1CCCC1>[CH2:1]([C:5]1[N:6]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[Cl:19])[C:7]([CH:10]([OH:11])[CH3:20])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazole-5-carboxaldehyde (1.1 g, 3.97 mmol) was dissolved in dry tetrahydrofuran (15 mL), cooled to -78° C. under argon, and a solution of methyl lithium (3.64 mL of 1.2M in diethyl ether, 4.57 mmol) was added dropwise. The mixture was stirred for 1.5 hours, quenched with ammonium chloride solution, warmed to ambient temperature and extracted with ethyl acetate. The washed, dried, concentrated product was flash chromatographed over silica gel with ethyl acetate to provide 1.07 g (92%) of 2-n-butyl-1-(2-chlorophenyl)methyl-5-(a-hydroxy)ethyl-1H-imidazole.

Workup

customquenched with ammonium chloride solution
temperaturewarmed to ambient temperature
extractionextracted with ethyl acetate
customThe washed, dried
customchromatographed over silica gel with ethyl acetate

Sources & evidence

ORD record: ord-939a167af7d5454aa71a6b49e4c03293
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05530017

Linked notes

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