Acetic Acid → 1-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole

HRID 1735829Notes

Reaction equation

HRID 1735829 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([O:28][CH3:29])=[O:27])=[CH:16][CH:15]=2)[C:7]([CH:11]=[O:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].CC(O)=O>C(O)C>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]([O:28][CH3:29])=[O:27])=[CH:16][CH:15]=2)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 156980691-(2'-Carbomethoxybiphenyl-4-yl)methyl-2-butyl-4-chloroimidazole-5-carboxaldehyde

Product 1

HCID 110041921-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-2-butyl-4-chloro-5-hydroxymethylimidazole

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 4.8 g of 2-butyl-4-chloro-5-formyl-1-[(2'-methoxycarbonyl-1,1'-biphenyl-4-yl)methyl]-1H-imidazole in 100 ml of absolute ethanol is added with a solution of 0.44 g of NaBH4 in 10 ml of ethanol. The mixture is stirred at room temperature for 1 hour then is acidified with glacial CH3COOH to pH 4. The resulting solution is evaporated to dryness under reduced pressure and the residue is taken up into ether. The in soluble part is filtered, the ether solution is evaporated to dryness and the residue is stripped more times with toluene.

Workup

  1. customThe resulting solution is evaporated to dryness under reduced pressure
  2. filtrationThe in soluble part is filtered
  3. customthe ether solution is evaporated to dryness

Sources & evidence

ORD record
ord-4c6f921d6cb74cdebb6522867fbdd0ae
Source dataset
uspto-grants-1996_07
Patent number
US05538987

Reaction notes

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