Acetone → HCID 54404886, compound

HRID 1595310Notes

Reaction equation

HRID 1595310 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([C:21](=[O:28])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[CH2:29][CH2:30][CH3:31])=[CH:7][CH:6]=1)[CH3:2].[BH4-].[Na+].CC(C)=O>C(O)C>[CH2:1]([O:3][C:4](=[O:32])[C:5]1[CH:6]=[CH:7][C:8]([CH2:11][N:12]2[C:16]3[CH:17]=[C:18]([CH:21]([OH:28])[C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH:19]=[CH:20][C:15]=3[N:14]=[C:13]2[CH2:29][CH2:30][CH3:31])=[CH:9][CH:10]=1)[CH3:2]

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydrideHCID 15546111HCID 15546111, compound

Product 1

HCID 54404886HCID 54404886, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 4-(6-benzoyl-2-propyl-benzoimidazol-1-ylmethyl)-benzoic acid ethyl ester (1.5 g; 3.5 mmol) in ethanol (50 mL) was added sodium borohydride (1.0 g; 29.4 mmol). After stirring at ambient temperature for 4 hours, acetone (20 mL) was added. The solvent was evaporated. The residue was dissolved in ethyl acetate and washed with water. The organic phase was evaporated to give the title compound (0.9 g, 60% yield) as a white solid which was used without further purification in step 2.

Workup

  1. customThe solvent was evaporated
  2. dissolutionThe residue was dissolved in ethyl acetate
  3. washwashed with water
  4. customThe organic phase was evaporated

Sources & evidence

ORD record
ord-2f9508c229e3454c988c5709b4d1eb6f
Source dataset
uspto-grants-2001_09
Patent number
US06288100B1

Reaction notes

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