Diethyl Ether → 1H-Imidazole-1-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-2-(3-(phenylmethoxy)propyl)-

HRID 1857780Notes

Reaction equation

HRID 1857780 reaction equation
C(O[CH2:9][CH2:10][C:11]1[N:12]([CH2:28][CH2:29][OH:30])[C:13]([S:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=1)C1C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:37]([O:39][CH2:40][CH3:41])C>O>[CH2:40]([O:39][CH2:37][CH2:9][CH2:10][C:11]1[N:12]([CH2:28][CH2:29][OH:30])[C:13]([S:19][C:20]2[CH:25]=[C:24]([Cl:26])[CH:23]=[C:22]([Cl:27])[CH:21]=2)=[C:14]([CH:16]([CH3:18])[CH3:17])[N:15]=1)[C:41]1[CH:24]=[CH:25][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 474087HCID 474087, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 4741011H-Imidazole-1-ethanol, 5-((3,5-dichlorophenyl)thio)-4-(1-methylethyl)-2-(3-(phenylmethoxy)propyl)-Yield 87%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 30 ml of dry diethyl ether was dissolved 3.0 g (5.8 mmol) of the ester (130d), to the mixture was added 220 mg (5.8 mmol) of lithium aluminium hydride under ice-cooling. The mixture was stirred at room temperature for 15 minutes. The reaction mixture was diluted with water and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate), and further recrystallized from n-hexane to provide 2.4 g (yield 87%) of 2-(2-(3-benzyloxypropyl)-5-(3,5-dichlorophenylthio)-4-isopropyl-1H-imidazol-1-yl)-ethanol (136e) as crystals. mp 104-106° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate)
  8. customfurther recrystallized from n-hexane

Sources & evidence

ORD record
ord-e6eb4e0ac1724bc7995ad4a1340a01a1
Source dataset
uspto-grants-2000_11
Patent number
US06147097

Reaction notes

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