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

반응식

HRID 260738 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-939a167af7d5454aa71a6b49e4c03293
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05530017

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