Sodium borohydride → [4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methanol

HRID 1661944Notes

Reaction equation

HRID 1661944 reaction equation
[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:16]=[CH:15][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:13][CH:12]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][C:3]=1[CH:26]=[O:27].[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[C:10]2[N:9]=[C:8]([C:11]3[CH:12]=[CH:13][C:14]([CH:17]([CH3:19])[CH3:18])=[CH:15][CH:16]=3)[N:7]([CH2:20][CH2:21][O:22][CH3:23])[C:6]=2[C:5]([O:24][CH3:25])=[CH:4][C:3]=1[CH2:26][OH:27]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 577720644-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde

Product 1

HCID 57771990[4-bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazol-5-yl]-methanolYield 88.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.08 g (4.82 mmol) of 4-Bromo-2-(4-isopropyl-phenyl)-7-methoxy-1-(2-methoxy-ethyl)-1H-benzoimidazole-5-carbaldehyde is dissolved in 60 ml Ethanol and NaBH4 (365 mg, 9.64 mmol) is added. After stirring for 30 min ice/water is added and the reaction mixture is extracted with ethyl acetate (3×). The organic layer is washed with water (3×) and brine (2×), dried (Na2SO4) and concentrated in vacuo. The residue is crystallized from diethyl ether/hexanes to give 1.85 g of colorless crystals.

Workup

  1. additionis added
  2. extractionthe reaction mixture is extracted with ethyl acetate (3×)
  3. washThe organic layer is washed with water (3×) and brine (2×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue is crystallized from diethyl ether/hexanes

Sources & evidence

ORD record
ord-e52cbef093e84631879f52233d99660d
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

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