Aluminium lithium hydride → 2-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanol

HRID 1416024Notes

Reaction equation

HRID 1416024 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[Cl:7][C:8]1[CH:9]=[C:10]([S:15][C:16]2[N:20]([CH3:21])[C:19]([CH2:22][C:23](OC)=[O:24])=[N:18][C:17]=2[CH:27]([CH3:29])[CH3:28])[CH:11]=[C:12]([Cl:14])[CH:13]=1>C(OCC)C>[Cl:14][C:12]1[CH:11]=[C:10]([S:15][C:16]2[N:20]([CH3:21])[C:19]([CH2:22][CH2:23][OH:24])=[N:18][C:17]=2[CH:27]([CH3:29])[CH3:28])[CH:9]=[C:8]([Cl:7])[CH:13]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54000775methyl [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]acetate

Product 1

HCID 4740102-(5-(3,5-Dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl)ethanolYield 82%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of 0.08 g (2.1 mmol)of lithium aluminium hydride in dry diethyl ether was added dropwise in nitrogen gas a solution of 0.766 g (2.05 mmol)of methyl [5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]acetate (33)in diethyl ether (10 ml)under ice-cooling over 10 minutes with stirring. The reaction mixture was stirred at the same temperature for 0.5 hours and at room temperature for 1 hour, and then, there was added ice-water. The ether layer was separated by decantation, and the aqueous layer was extracted with diethyl ether. The ether extracts were combined, dried over magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from isopropyl ether, and filtered to give 0.58 g of 2-[5-(3,5-dichlorophenylthio)-4-isopropyl-1-methyl-1H-imidazol-2-yl]ethanol (Compound I-81a)(yield 82%).

Workup

  1. temperaturecooling over 10 minutes
  2. stirringThe reaction mixture was stirred at the same temperature for 0.5 hours and at room temperature for 1 hour
  3. customThe ether layer was separated by decantation
  4. extractionthe aqueous layer was extracted with diethyl ether
  5. dry with materialdried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was recrystallized from isopropyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-259891ab607c4dda82d208d9f6e2b275
Source dataset
uspto-grants-1999_06
Patent number
US05910506

Reaction notes

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