Water → HCID 22058647, compound

HRID 1828822Notes

Reaction equation

HRID 1828822 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([CH3:23])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=2[Cl:22])[C:6]=1[CH:7]=[O:8].[BH4-].[Na+].O>C(O)C>[Cl:1][C:2]1[N:3]=[C:4]([CH3:23])[N:5]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:12][C:11]=2[Cl:22])[C:6]=1[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 22058630HCID 22058630, compound

Product 1

HCID 22058647HCID 22058647, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-1-(2-chloro-4-(1-pentyloxy)benzyl)-2-methyl-1H-imidazole-5-carbaldehyde (1.05 g) was dissolved in ethanol (10 ml), and sodium borohydride (168 mg) was added under ice-cooling. The mixture was stirred at room temperature for 3 hr. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. To the residue was added hexane (10 ml) and the precipitated crystals were collected by filtration and dried by heating under reduced pressure to give 4-chloro-1-(2-chloro-4-(1-pentyloxy)benzyl)-5-hydroxymethyl-2-methyl-1H-imidazole (786 mg) as colorless crystals.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionTo the residue was added hexane (10 ml)
  7. filtrationthe precipitated crystals were collected by filtration
  8. customdried
  9. temperatureby heating under reduced pressure

Sources & evidence

ORD record
ord-fce1d938d1a24ac681c228ebad2a49dd
Source dataset
uspto-grants-2006_06
Patent number
US07060721B1

Reaction notes

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