Tetrahydrofuran → 2-n-butyl-1-(2-chlorophenyl)methyl-5-(a-hydroxy) ethyl-1H-imidazole

HRID 36973Notes

Reaction equation

HRID 36973 reaction equation
[CH2:1]([C:5]1(C=O)[NH:9][CH:8]=[CH:7][N:6]1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])[CH2:2][CH2:3][CH3:4].C[Li].[O:22]1CC[CH2:24][CH2:23]1>>[CH2:1]([C:5]1[N:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[C:7]([CH:23]([OH:22])[CH3:24])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 86746468HCID 86746468, compoundHCID 178418348HCID 178418348, compound

Product 1

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

Conditions

Temperature
-78 °C

Procedure

A solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H- imidazol-carboxaldehyde (Example 1 (iii)) (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 flashed 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

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

Sources & evidence

ORD record
ord-2104a6d98e3e474cb37e3f1c0890a857
Source dataset
uspto-grants-1995_05
Patent number
US05418250

Reaction notes

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