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

反応式

HRID 260738 の反応式
[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]

参加物

4

反応物 2

HCID 101075301H-Imidazole-5-carboxaldehyde, 2-butyl-1-[(2-chlorophenyl)methyl]-HCID 178418348HCID 178418348、化合物

生成物 1

HCID 104244542-n-butyl-1-(2-chlorophenyl)methyl-5-(a-hydroxy) ethyl-1H-imidazole収率 92%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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.

後処理

  1. customquenched with ammonium chloride solution
  2. temperaturewarmed to ambient temperature
  3. extractionextracted with ethyl acetate
  4. customThe washed, dried
  5. customchromatographed over silica gel with ethyl acetate

出典と根拠

ORDレコード
ord-939a167af7d5454aa71a6b49e4c03293
出典データセット
uspto-grants-1996_06
特許番号
US05530017

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